The important role of 22236-08-4

The synthetic route of 22236-08-4 has been constantly updated, and we look forward to future research findings.

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 22236-08-4, name is 3-(Difluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 3-(Difluoromethoxy)aniline

General procedure: Step-1:4-amino-2,6-dichloro pyrimidine: 2,4,6-trichloro pyrimidine (1.0 mmol) in ethanol (5 mL) was treated with an aromatic amine (1.1 mmol) in the presence of Na2CO3 (1.1 mmol) at rt. The mixture was stirred at reflux for 2-4 h until completion of the reaction. The reaction progress was followed by TLC. After completion of the reaction, an equal volume of water was added with cooling. The resulting white precipitate was filtered, washed with water, and dried in vacuum over night to yield 4-substituted 2,6-dichloro pyrimidine. In case of no precipitation, ethanol was removed by rota vap., and the residue was dissolved in CH2Cl2. The organic layer was washed twice with water, brine, dried (Na2SO4), filtered, and concentrated. The resulting crude was purified by column chromatography to afford the 4-amino-2,6-dichloro pyrimidines in 85-95% yield. Step-2: 2,4-diamino-6-chloropyrimidine: 4-amino-2,6-dichloro pyrimidine (1.0 mmol) prepared from the above procedure was treated with another aliphatic amine or aromatic amine (2.0 mmol) in the presence of DIEPA (5.0 mmol) in n-BuOH (5 mL) at rt. For an aliphatic amine the reaction mixture was stirred at rt for overnight. For an aromatic amine the reaction mixture was refluxed for 24-72 h or placed in microwave (150 C, 2-7 h) until completion of the reaction. The reaction progress was followed by TLC. After completion of the reaction, solvents were removed by rota vap., and the residue was dissolved in CH2Cl2. The organic layer was washed twice with water, brine, dried (Na2SO4), filtered, and concentrated. The resulting crude was purified by column chromatography (EtOAc/hexane) to afford the 2,4-diammino-6-chloropyrimidines in 85-90% yield. Step-3: 2,4,6-triaminopyrimidine: 2,4-diamino-6-chloropyrimidine (1.0 mmol) prepared from the above procedure was treated with another suitable aliphatic amine or aromatic amine (3.0 mmol). For an aliphatic amine, 2,4-diamino-6-chloropyrimidine (1.0 mmol) was treated with aliphatic amine (3.0 mmol) and DIPEA (5.0 mmol) in n-BuOH (5 mL) and placed in microwave (150 C) for 3-7 h. After the completion of the reaction (monitored by TLC), solvents were removed and the residue was dissolved in EtOAc. The organic layer was washed twice with water, brine, dried (Na2SO4), filtered, and concentrated. The resulting crude was purified by column chromatography to afford the 2,4,6-triaminopyrimidines 90-95% yield. For aromatic amine; 2,4-diamino-6-chloropyrimidine (1.0 equiv) was dissolved in dioxane under argon and to that were added Pd2(dba)3 (10 mol %), Xantphos (10 mol %), aromatic amine (1.2 mmol), t-BuOK (1.2 mmol). The resulting solution was degassed with argon for 5 min and heated to 85 C for overnight. The reaction mixture was filtered through a pad of celite, washed with CH2Cl2 (2 × 10 mL) and the resulting filtrate was concentrated. The resulting crude was purified by flash column chromatography to yield 2,4,6-triaminopyrimidines in 90-95% yield.

The synthetic route of 22236-08-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sagi, Vasudeva Naidu; Liu, Tianyu; Lu, Xiaoying; Bartfai, Tamas; Roberts, Edward; Bioorganic and Medicinal Chemistry Letters; vol. 21; 23; (2011); p. 7210 – 7215;,
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New downstream synthetic route of 22236-08-4

The synthetic route of 3-(Difluoromethoxy)aniline has been constantly updated, and we look forward to future research findings.

These common heterocyclic compound, 22236-08-4, name is 3-(Difluoromethoxy)aniline, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Quality Control of 3-(Difluoromethoxy)aniline

A solution of 4-chloro-6-nitro-2- (pyrazin-2-yl) quinazoline (1.00 g, crude, 3.7 mmol, 1.0 equiv), 3- (difluoromethoxy) benzenamine 600 mg, 3.7 mmol, 1.0 eq) and Et 3 N (1.00 g, 10 mmol, 3.0 eq) was stirred at 75 C. for 18 h. After cooling, the volatiles were removed in vacuo and the residue was washed with H 2 O (100 mL × 2). The solid was dried in vacuo to give 1.40 g of N- (3- (difluoromethoxy) phenyl) -6-nitro-2- (pyrazin-2-yl) quinazolin-4-amine as a black solid 90.2% at the stage). LCMS m / z = 411.0 (M + 1) (Method A) (retention time = 1.61 min).

The synthetic route of 3-(Difluoromethoxy)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OTSUKA PHARMACEUTICAL COMPANY LIMITED; SUZUKI, MASAKI; KONDO, KAZUMI; KURIMURA, MUNEAKI; VALLURU, KRISHNA REDDY; TAKAHASHI, AKIRA; KURODA, TAKESHI; TAKAHASHI, HARUKA; FUKUSHIMA, TAE; MIYAMURA, SHIN; GHOSH, INDRANATH; DOGRA, ABHISHEK; HARRIMAN, GERALDINE; ELDER, AMY; SHIMIZU, SATOSHI; HODGETTS, KEVIN J; NEWCOM, JASON S; (678 pag.)JP6121658; (2017); B2;,
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Brief introduction of C7H7F2NO

According to the analysis of related databases, 22236-08-4, the application of this compound in the production field has become more and more popular.

Reference of 22236-08-4, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 22236-08-4 as follows.

Intermediate.11 rac-Allyl [l -{N’-cyano-N-[3-(difluoromethoxy)phenyl]carbamimidoyl} -3-(3,4-dichlorophenyl)-4,5- dihydro- l//-pyrazol-4-yl]carbamate To a stirred solution of m-difluoromethoxy aniline, 8.20 ml. (65.5 mmol) in anhydrous tetrahydrofuran (100 mL) at -78 C was added n -butyl lithium, 33.0 mL (65.5 mmol, 2 M in hexane) dropwise, while maintaining the reaction temperature below -65 C during the addition. The reaction mixture was stirred for 1 hour at -78 C before rac-phenyl 4-{[(ailyioxy)carbonyl]amino}-N-cyano-3-(3,4- dichlorophenyl)-4,5-dihydro- 1 H-pyrazole- 1 -carboximidate (intermediate 9), 10.0 g (21.8 mmol) in anhydrous tetrahydrofuran (600 mL) was added dropwise maintaining the reaction temperature below -65 C. The reaction mixture was stirred for 2 hours at -78 C before slowly pouring over saturated ammonium chloride solution (700 mL). The crude product was extracted into ethyl acetate (700 mL) and the organic layers were combined and washed with brine solution (350 mL). The collected organic phase was dried over magnesium sulfate, filtered and the solvent evaporated to yield an off-white crude solid. The crude solid was precipitated from a minimum volume of ethyl acetate, filtered, and washed with diethyl ether to yield rac-allyl [ 1 – {N’-cyano-N- [3 – (difluoromethoxy)phenyi]carbamimidoyl}-3-(3,4-dichlorophenyl)-4,5-dihydro-lH-pyrazoi-4- yl] carbamate, 7.6 g (67%) as a white solid. NM R (400 MHz, DMSO-d6): delta [ppm] = 4.08 (dd, 1H), 4.36-4.53 (m, 3H), 5.11 (dd, 1H), 5.17 (dd, 1H), 5.50-5.59 (m, 1H), 5.77-5.90 (m, 1H), 6.99 (dd, 1H), 7.16 (t, 1H), 7.21 (t, 1H), 7.23 (dd, 1H), 7.39 (t, 1H), 7.73-7.81 (m, 2H), 8.15 (d, 1H), 8.17 (d, 1H), 9.79 (br s, 1H). I MS (method 3): Rt = 1.78 min MS (ESI): [M + Hf = 523.2

According to the analysis of related databases, 22236-08-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; STELLFELD, Timo; MOWAT, Jeffrey Stuart; STRESEMANN, Carlo; HILLIG, Roman; KOeHR, Silke; STOeCKIGT, Detlef; WEISKE, Joerg; HARTUNG, Ingo; BARAK, Naomi; CHRIST, Clara; TER LAAK, Antonius; BADOCK, Volker; CRAMPTON, Rosemary Helen; STEFANUTI, Ian; (194 pag.)WO2016/166186; (2016); A1;,
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Brief introduction of C7H7F2NO

According to the analysis of related databases, 22236-08-4, the application of this compound in the production field has become more and more popular.

Reference of 22236-08-4, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 22236-08-4 as follows.

Intermediate.11 rac-Allyl [l -{N’-cyano-N-[3-(difluoromethoxy)phenyl]carbamimidoyl} -3-(3,4-dichlorophenyl)-4,5- dihydro- l//-pyrazol-4-yl]carbamate To a stirred solution of m-difluoromethoxy aniline, 8.20 ml. (65.5 mmol) in anhydrous tetrahydrofuran (100 mL) at -78 C was added n -butyl lithium, 33.0 mL (65.5 mmol, 2 M in hexane) dropwise, while maintaining the reaction temperature below -65 C during the addition. The reaction mixture was stirred for 1 hour at -78 C before rac-phenyl 4-{[(ailyioxy)carbonyl]amino}-N-cyano-3-(3,4- dichlorophenyl)-4,5-dihydro- 1 H-pyrazole- 1 -carboximidate (intermediate 9), 10.0 g (21.8 mmol) in anhydrous tetrahydrofuran (600 mL) was added dropwise maintaining the reaction temperature below -65 C. The reaction mixture was stirred for 2 hours at -78 C before slowly pouring over saturated ammonium chloride solution (700 mL). The crude product was extracted into ethyl acetate (700 mL) and the organic layers were combined and washed with brine solution (350 mL). The collected organic phase was dried over magnesium sulfate, filtered and the solvent evaporated to yield an off-white crude solid. The crude solid was precipitated from a minimum volume of ethyl acetate, filtered, and washed with diethyl ether to yield rac-allyl [ 1 – {N’-cyano-N- [3 – (difluoromethoxy)phenyi]carbamimidoyl}-3-(3,4-dichlorophenyl)-4,5-dihydro-lH-pyrazoi-4- yl] carbamate, 7.6 g (67%) as a white solid. NM R (400 MHz, DMSO-d6): delta [ppm] = 4.08 (dd, 1H), 4.36-4.53 (m, 3H), 5.11 (dd, 1H), 5.17 (dd, 1H), 5.50-5.59 (m, 1H), 5.77-5.90 (m, 1H), 6.99 (dd, 1H), 7.16 (t, 1H), 7.21 (t, 1H), 7.23 (dd, 1H), 7.39 (t, 1H), 7.73-7.81 (m, 2H), 8.15 (d, 1H), 8.17 (d, 1H), 9.79 (br s, 1H). I MS (method 3): Rt = 1.78 min MS (ESI): [M + Hf = 523.2

According to the analysis of related databases, 22236-08-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; STELLFELD, Timo; MOWAT, Jeffrey Stuart; STRESEMANN, Carlo; HILLIG, Roman; KOeHR, Silke; STOeCKIGT, Detlef; WEISKE, Joerg; HARTUNG, Ingo; BARAK, Naomi; CHRIST, Clara; TER LAAK, Antonius; BADOCK, Volker; CRAMPTON, Rosemary Helen; STEFANUTI, Ian; (194 pag.)WO2016/166186; (2016); A1;,
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Discovery of 22236-08-4

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 22236-08-4, its application will become more common.

Some common heterocyclic compound, 22236-08-4, name is 3-(Difluoromethoxy)aniline, molecular formula is C7H7F2NO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Application In Synthesis of 3-(Difluoromethoxy)aniline

General procedure: Atwo neck round bottom flask under argon equipped with a condenser was chargedwith aldehyde 4 (1.0 mmol, 1.0 equiv.)and 4-chloroaniline 3b (1.1 mmol, 1.1equiv.) in 2-pentanol (3.3 mL, 0.3 M) and stirred at reflux for two hours. Thetetronic acid 5 (1.1 mmol, 1.1 equiv.)in 2-pentanol (0.8 mL) was then added at reflux, after 10 mins. The thirdcomponent aniline 3 (1.0 mmol, 1.0 equiv.)was added dropwise and was refluxed for 30 min. The solvent was evaporated under vacuum and theproduct purified by recrystallization in ethanol (5.0 mL) or by flashchromatography

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 22236-08-4, its application will become more common.

Reference:
Article; Jeedimalla, Nagalakshmi; Johns, Jennifer; Roche, Stephane P.; Tetrahedron Letters; vol. 54; 44; (2013); p. 5845 – 5848;,
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Extended knowledge of 22236-08-4

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 22236-08-4, name is 3-(Difluoromethoxy)aniline, A new synthetic method of this compound is introduced below., SDS of cas: 22236-08-4

General procedure: A two neck round bottom flask under argon equipped with acondenser was charged with aldehyde 4 (1.0 equiv.) and 4-chloroaniline 3l (1.1 equiv.) in 2-pentanol [0.3 M] and stirred atreflux for 2 h. The tetronic acid 5 (1.1 equiv.) in 2-pentanol (minimumamount) was then added at reflux. After another 10 min atreflux, the third component aniline 3 (1.0 equiv.) was added neat.The reaction mixture was refluxed for an additional 30 min. Allvolatiles were evaporated under vacuum and the crude product purified by recrystallization in ethanol or by flash chromatographyon silica gel

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Jeedimalla, Nagalakshmi; Flint, Madison; Smith, Lyndsay; Haces, Alberto; Minond, Dmitriy; Roche, Stephane P.; European Journal of Medicinal Chemistry; vol. 106; (2015); p. 167 – 179;,
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Introduction of a new synthetic route about 22236-08-4

The synthetic route of 22236-08-4 has been constantly updated, and we look forward to future research findings.

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 22236-08-4, name is 3-(Difluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 22236-08-4

Intermediate 37 rac-Allyl [ 1 – {N’-cyano-N- [3 -(difluoromethoxy)phenyl] carbamimidoyl }-3-(3 ,4-dichloroph( dihydro-l/7-pyrazol-4-yl]methylcarbamate To a stirred solution of w-difluoromethoxy aniline, 10.1 g (6.35 mmol) in anhydrous tetrahydrofuran (30 mL) at -60 C under a nitrogen atmosphere was added lithium diisopropylamide, 3.2 l. (6.35 mmol, 2 M in tetrahydrofuran) . The reaction mixture was stirred for 30 min at -60 C before adding rac- phenyl 4-{[(ailyioxy)carbonyl](methyl)amino}-N-cyano-3-(3,4-dichiorophenyl)-4,5-dihydro-lH- pyrazole- 1 -carboximidate (intermediate 36) 1.0 g (2.12 mmol), in tetrahydrofuran (10 mL). The reaction mixture was stirred for 30 min at -60C and 1 h at room temperature. The reaction mixture was quenchend with water, then poured into brine and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the solvent evaporated. The residue was purified by column chromatography on a NH- silica phase (eluent: hexane/ethyl acetate) to yield rac-allyl [1-{Nu’- cyano-N-[3-(difluoromethoxy)phenyl]carbamimidoyl}-3-(3,4-dichlorophenyl)-4,5-dihydro-lH- pyrazol-4-yl]methylcarbamate, 875 mg (77%) as a beige oil. LCMS (method 2): R, = 1.36 min MS (ESI): [M + Hf = 536.8

The synthetic route of 22236-08-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; STELLFELD, Timo; MOWAT, Jeffrey Stuart; STRESEMANN, Carlo; HILLIG, Roman; KOeHR, Silke; STOeCKIGT, Detlef; WEISKE, Joerg; HARTUNG, Ingo; BARAK, Naomi; CHRIST, Clara; TER LAAK, Antonius; BADOCK, Volker; CRAMPTON, Rosemary Helen; STEFANUTI, Ian; (194 pag.)WO2016/166186; (2016); A1;,
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Share a compound : 3-(Difluoromethoxy)aniline

The synthetic route of 22236-08-4 has been constantly updated, and we look forward to future research findings.

Electric Literature of 22236-08-4, A common heterocyclic compound, 22236-08-4, name is 3-(Difluoromethoxy)aniline, molecular formula is C7H7F2NO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: A solution of cyanic bromide [Caution, highly toxic] (2 equiv) in diethyl ether (10 mL) was added dropwise to a solution of the appropriately substituted aniline (1 equiv) in diethyl ether (10 mL) at 0 C. After complete addition the mixture was warmed to ambient temperature and stirred 1-20 h, which was followed by TLC. Solids were filtrated and washed with ether. The filtrate was washed with 1 M HCl (25 mL) followed by brine (25 mL). The organic layer was collected, dried over anhydrous MgSO4, filtrated and evaporated to dryness under reduced pressure. 5.1.32 N-(3-(Difluoromethoxy)phenyl)cyanamide (24h) The reaction of 3-(difluoromethoxy)aniline (23h) (1.60 g, 10.0 mmol) according to procedure A yielded, after purification over silica with ethyl acetate/petroleum ether (60-80) (25/75, v/v), the title compound as a light brown oil which solidified upon standing (683 mg, 3.71 mmol, 37%); Rf 0.24 (ethyl acetate/petroleum ether (60-80), 25/75, v/v). 1H NMR (CDCl3) delta 7.31-7.22 (m, 2H, HAryl), 6.87-6.76 (m, 2H, HAryl), 6.77 (s, 1H, NH), 6.48 (t, JHF = 73.5 Hz, 1H, CHF2). 13C NMR (CDCl3) delta 152.30 (Ar-O), 138.96 (Ar-N), 131.18 (Ar), 117.84 (t, CHF2, JCF = 260.72 Hz), 114.37 (Ar), 112.48 (Ar), 111.13 (NCN), 107.24 (Ar).

The synthetic route of 22236-08-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Klein, Pieter J.; Christiaans, Johannes A.M.; Metaxas, Athanasios; Schuit, Robert C.; Lammertsma, Adriaan A.; Van Berckel, Bart N.M.; Windhorst, Albert D.; Bioorganic and Medicinal Chemistry; vol. 23; 5; (2015); p. 1189 – 1206;,
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Sources of common compounds: 22236-08-4

The synthetic route of 22236-08-4 has been constantly updated, and we look forward to future research findings.

22236-08-4, name is 3-(Difluoromethoxy)aniline, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 22236-08-4

To a solution of 3- (difluoromethoxy) aniline (318 mg, 2.0 iranol) and pyridine (633 mg, 8.0 iranol) in N-methylpyrrolidone (2 mL) was added phenyl chloroformate (251 muL, 2.0 mmol) under ice-cooling, and the mixture was stirred at room temperature for 2 hr. 2-chloro-4- [ (5-methyl-5H-pyrrolo [3, 2-d]pyrimidin-4- yl) oxy] aniline (275 mg, 1.0 mmol) was added to the reaction mixture, and the mixture was stirred at 800C for 8 hr. The reaction mixture was diluted with water, basified with IN aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and concentrated under reduced pressure. The residue was purified by NH silica gel column chromatography (hexane/ethyl acetate=80/20->0/100) , and then silica gel column chromatography (hexane/ethyl acetate=80/20-»0/100) and recrystallized from diisopropyl ether to give the title compound (229 mg, 50%) as a white solid. 1H-NMR (DMSO-de, 300 MHz) delta 4.11 (3H, s) , 6.61 (IH, d, J = 3.0 Hz), 6.81 (IH, dd, J = 8.0, 2.1 Hz), 7.19 – 7.23 (IH, m) , 7.22 (IH, t, J = 74.1 Hz), 7.31 (IH, dd, J = 9.0, 2.7 Hz), 7.35 (IH, t, J = 8.0 Hz), 7.49 (IH, t, J = 2.1 Hz), 7.56 (IH, d, J = 2.7 Hz), 7.80 (IH, d, J = 3.0 Hz), 8.17 (IH, d, J = 9.0 Hz), 8.30 (IH, s), 8.43 (IH, br s) , 9.60 (IH, br s) .

The synthetic route of 22236-08-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2007/4749; (2007); A1;,
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The important role of C7H7F2NO

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Adding a certain compound to certain chemical reactions, such as: 22236-08-4, name is 3-(Difluoromethoxy)aniline, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 22236-08-4, HPLC of Formula: C7H7F2NO

EXAMPLE 2 Preparation of 2,3-dichloro-N-(m-difluoromethoxyphenyl)maleimide 16.7 g (0.1 mole) of 2,3-dichloromaleic anhydride is dissolved in 100 ml of dioxane, and a solution of 15.9 g (0.1 mole) of m-difluoromethoxyaniline in 30 ml of dioxane is added dropwise to it at room temperature over 20 minutes with stirring. Thereafter, the resulting solution is stirred at 70-80 C. for 2 hours and the dioxane is then distilled off under a reduced pressure. Water is added to the residue to precipitate crystals. The precipitated crystals are filtered off and recrystallized to give 29.2 g (yield: 95%) of 2,3-dichloro-N-(m-difluoromethoxyphenyl)maleimide melting at 122-124 C. in the form of light yellow plate crystals.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Showa Denko Kabushiki Kaisha; US4455315; (1984); A;,
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