Tag: M.W=200-300

Synthetic Route of 887267-47-2, 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. 887267-47-2, name is 2-Bromo-5-(trifluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

An aqueous solution of NaOH (10.2 g, 254 mmol in 20 mL water) was added to a solution of Preparation 67A in t-butanol (100 mL). Next, a solution of di- tert-butyldicarbonate (60.1 mL, 254 mmol) in t-butanol was added at room temperature and the resulting mixture was stirred for 4 days. The reaction mixture became a suspension and was filtered. The residue was washed with a small amount of water. The filtrate was concentrated to half its volume and then extracted with EtOAc (2 x 200 mL). The organic layer was washed with brine solution and dried over anhydrous Na2SO4. Removal of solvent in vacuo gave Preparation 67B (31.0 g) as a white solid.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Bromo-5-(trifluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2009/3077; (2008); A1;,
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Related Products of 439814-87-6,Some common heterocyclic compound, 439814-87-6, name is 4-Bromo-1-(dimethoxymethyl)-2-fluorobenzene, molecular formula is C9H10BrFO2, 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.

To a solution of 4-bromo-1-dimethoxymethyl-2-fluorobenzene (4.53 g, 18.2 mmol) in tetrahydrofuran (50 mL) were added n-butyllithium (1.6 mol/L in hexanes; 15 mL) and dimethylformamide (2.1 mL, 27 mmol) sequentially at -78 C. under nitrogen atmosphere, and the mixture was stirred for 15 min. Water was added, and the mixture was extracted twice with ether. The organic layer was combined, washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography (6:1 Hexane/ethyl acetate) to afford 4-dimethoxymethyl-3-fluorobenzaldehyde (2.26 g, 63%). 1H NMR (400 MHz, CDCl3) delta (ppm) 3.36 (s, 6H), 5.61 (s, 1H), 7.53 (dd, J=9.8, 1.6 Hz, 1H), 7.65 (dd, J=7.8, 1.6 Hz, 1H), 7.73 (t, J=7.8 Hz, 1H), 9.95 (d, J=2.0 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-1-(dimethoxymethyl)-2-fluorobenzene, its application will become more common.

Reference:
Patent; Akama, Tsutomu; Holcomb, Ryan; Tolman, Richard L.; US2002/120144; (2002); A1;,
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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. 887267-47-2, name is 2-Bromo-5-(trifluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 2-Bromo-5-(trifluoromethoxy)aniline

Reference Example 1-1N-(2-Bromo-5-trifluoromethoxyphenyl)-2,2,2-trifluoroacetamide Under ice-cooling, to a solution of 2-bromo-5-trifluoromethoxyaniline (0.98 g) in tetrahydrofuran (10 mL) were added trifluoroacetic anhydride (0.79 mL) and pyridine (0.61 mL). The solution was stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure. To the residue was added ethyl acetate, and the organic layer was washed with 10% aqueous citric acid solution, a saturated aqueous sodium hydrogen carbonate solution, and saturated brine successively, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the obtained crude product was purified by silica gel column chromatography (eluting solvent: hexane-ethyl acetate) to obtain the title compound (1.30 g).1H-NMR (CDCl3) delta ppm: 8.60-8.30 (2H, m), 7.65 (1H, d, J=8.9 Hz), 7.10-7.00 (1H, m)

The synthetic route of 887267-47-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KISSEI PHARMACEUTICAL CO., LTD.; US2012/122931; (2012); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 104566-41-8, name is (3-(Benzyloxy)phenyl)methanamine hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., category: ethers-buliding-blocks

EXAMPLE 1A 4-Chloro-5-(3-benzyloxybenzylamino)-2-i-propyl-3-(2H)pyridazinone (Compound No. 95) STR61 A mixture comprising 8.24 g of 3-benzyloxybenzylamine hydrochloride prepared in Reference Example 2A, 3.11 g of 2-i-propyl-4,5-dichloro-3(2H)pyridazinone, 7.26 g of potassium carbonate, 30 ml of 1,4-dioxane and 90 ml of water was refluxed under stirring for 4.5 hours. The majority of 1,4-dioxane was distilled off under reduced pressure, and the residue was extracted with ethyl acetate. The extract was washed with diluted hydrochloric acid, and then treated with cerite to remove the precipitate. The organic layer was separated, and washed with water and a saturated sodium chloride aqueous solution, and then dried over sodium sulfate. Then, the solvent was distilled off. The pale yellow oily substance thereby obtained was crystallized from ether-n-hexane to obtain 2.51 g of the above identified compound having a melting point of from 106 to 108 C. as colorless crystals. NMR(CDCl3)6: 7.48 (1H, s), 7.30 (5H, s), 7.3-6.7 (4H, m), 5.02 (2H, s), 4.49, 4.40 (total 2H, each s), 5.2-4.8 (1H, broad s), 1.30 (6H, d). MS (m/e): 383(M+), 348, 91 (100%).

According to the analysis of related databases, 104566-41-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nissan Chemical Industries Ltd.; US5098900; (1992); A;,
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Adding a certain compound to certain chemical reactions, such as: 33839-11-1, name is 4-Bromo-2-ethyl-1-methoxybenzene, 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 33839-11-1, Quality Control of 4-Bromo-2-ethyl-1-methoxybenzene

178.1 A solution of 4-bromo-2-ethyl-1-methoxybenzene (J. Chem. Soc., Perkin Trans. 1, 1987, 1423; 2.13 g, 9.9 mmol) in THF (30 ml) was cooled to -78 C. A 1.6M solution of n-BuLi in hexane (7.42 ml, 11.9 mmol) was added slowly and the mixture was stirred for 1.5 h. at -78 C. The mixture was warmed slowly to -10 C. and subsequently again cooled to -78 C. DMF (2.29 ml, 29.7 mmol) was added slowly and the mixture was stirred for 1 h. at -78 C. and for 1 h. at 0 C. The reaction mixture was poured into ice-cold 3M HCl and extracted with diethyl ether. The organic phase was dried and filtered, and the filtrate was concentrated. The residue was purified by chromatography (SiO2, hexane/EtOAc 8_1=>2:1). There were obtained 690 mg (42%) of 3-ethyl-4-methoxy-benzaldehyde as a yellowish liquid.

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; Ackermann, Jean; Alig, Leo; Chucholowski, Alexander; Groebke, Katrin; Hilpert, Kurt; Kuehne, Holger; Obst, Ulrike; Weber, Lutz; Wessel, Hans P.; US2001/1799; (2001); A1;,
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Synthetic Route of 439814-87-6, A common heterocyclic compound, 439814-87-6, name is 4-Bromo-1-(dimethoxymethyl)-2-fluorobenzene, molecular formula is C9H10BrFO2, 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.

Step 2 4-(4-Acetylpiperazin-l-yl)-2-fluorobenzaldehyde Palladium(II) acetate (111 mg, 0.49 mmol), 2-dicyclohexylphosphino-2′,6′-di-i-propoxy- Iota,Gamma-biphenyl (469 mg, 0.98 mmol) and sodium teri-butoxide (4.88 g, 49.2 mmol) were combined and the flask was purged with nitrogen. A solution of 1-piperazin-l-ylethanone (4.1 g, 32 mmol) and 4-bromo-l-(dimethoxymethyl)-2-fluoro-benzene (6.13 g, 24.6 mmol) in 1,4-dioxane (82 mL) was then added and the reaction was stirred at 100 C for 16 hours. The reaction was then filtered through diatomaceous earth and concentrated. The resulting residue was dissolved in 50 mL of THF and 50 mL of 1 N aqueous HC1 was added and the reaction was stirred at ambient temperature for 16 hours. The reaction was then neutralized with saturated aqueous Na2C03 and extracted with dichloromethane (x3), dried with MgSC>4, concentrated and purified by silica gel column chromatography (0-10% methanol in dichloromethane) to give 4-(4-acetylpiperazin-l-yl)-2-fluoro- benzaldehyde (3.68 g, 60% yield). LCMS (m/z) ES+251 [M+l]+.

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:
Patent; F. HOFFMANN-LA ROCHE AG; FAUBER, Benjamin; RENE, Olivier; WO2013/92941; (2013); A1;,
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These common heterocyclic compound, 104566-41-8, name is (3-(Benzyloxy)phenyl)methanamine hydrochloride, 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. name: (3-(Benzyloxy)phenyl)methanamine hydrochloride

N(3-benzyloxy-benzyl)-4-biphenylacetamide; To a solution of 4-biphenyl acetic acid (2.29 g, 10.45 mmol) in dimethylformamide, DMF, (30 ml) was added diisopropylethylamine, DIEA, (5.47 ml, 31.35 mmol) and stirred at room temperature for 15 min, then benzotriazolyloxy-tris[pyrrolidino]-phosphonium hexafluorophosphate, PyBOP, (5.43 g, 10.45 mmol) was added and the stirring was continued for further 30 min, then 3-benzyloxybenzylaminehydrochloride (2.6 g, 10.45 mmol) was added and the stirring continued for 24 hrs. The reaction mixture was then poured on to ice cooled water acidified with (10 ml) 1 N HCl and extracted with ethyl acetate (100 ml) and the organic layer washed with saturated solution of NaHCO3, water and brine, dried over Na2SO4 and the solvent removed under vacuum to give a yellowish-white powder of the desired compound (2.65 g) 62% yield.

The synthetic route of (3-(Benzyloxy)phenyl)methanamine hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hangauer, David G.; US2006/160800; (2006); A1;,
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92028-21-2, name is 6-Methoxy-[1,1′-biphenyl]-3-amine hydrochloride, 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. COA of Formula: C13H14ClNO

d. Synthesis of N-{2-[4-(3-phenyl-4-methoxyphenyl)aminophenyl]ethyl}-(R)-2-tert-butyldimethylsilyl-2-(8-benzyloxy-2(1H)-quinolinon-5-yl)ethylamine (NN); To compound JJ hydrochloride (73.7 g, 114 mmol) and 4-methoxy-3-phenylaniline hydrochloride (32.4 g, 137 mmol), toluene (380 mL) was added with mild agitation for 5 minutes, followed by sodium tert-butoxide (49.3 g, 513 mmol) in portions over 1 minute, and finally 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (10.65 g, 17 mmol) and tris(dibenzylideneacetone)dipalladium(0) (5.22 g, 5.7 mmol). The resulting mixture was stirred and heated to 85-89 C. (internal) for 2.5 hours. The solution was cooled to room temperature, water (400 ml) was added and the mixture was stirred for 5 minutes, filtered through Celite (80 g), and partitioned with toluene (100 ml). The organic layer was collected and concentrated under reduced pressure in a 40 C. bath to give N-{2-[4-(3-phenyl-4-methoxyphenyl)aminophenyl]ethyl}-(R)-2-tert-butyldimethylsilyl-2-(8-benzyloxy-2(1H)-quinolinon-5-yl)ethylamine (NN) as a dark viscous oil.

The synthetic route of 92028-21-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Axt, Sabine; Stergiades, Ioanna; US2004/224982; (2004); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1000574-79-7, name is 2-Bromo-4-(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 1000574-79-7, Recommanded Product: 1000574-79-7

Into a 250-mL round-bottom flask purged with and maintained under nitrogen was placed 2- bromo-4-(difluoromethoxy)benzenamine (7.9 g, 33.2 mmol), dioxane (100 mL), water (10 mL), CS2CO3 (32.46 g, 99.63 mmol), 4,4,5,5-tetramethyl-2-(prop-l-en-2-yl)-l,3,2-dioxaborolane (8.36 g, 49.8 mmol), and Pd(dppf)Cl2 (1.21 g, 1.65 mmol). The resulting solution was stirred overnight at 90C. The solids were filtered out. The filtrate was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with a gradient of ethyl acetate/petroleum ether (1 :30 to 1 :20). This resulted in 5.3 g (80%) of the title compound as a yellow solid. MS-ESI: 200.1 (M+l).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Bromo-4-(difluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; IFM TRE, INC.; GLICK, Gary; ROUSH, William R.; VENKATRAMAN, Shankar; SHEN, Dong-Ming; GHOSH, Shomir; KATZ, Jason; SEIDEL, Hans Martin; FRANCHI, Luigi; WINKLER, David Guenther; OPIPARI JR., Anthony William; (783 pag.)WO2019/23147; (2019); A1;,
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Synthetic Route of 38603-09-7, A common heterocyclic compound, 38603-09-7, name is 1,3-dibromo-2-methoxybenzene, molecular formula is C7H6Br2O, 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.

Example 21 Preparation of (3-Bromo-2-methoxyphenyl)-(2-methoxyphenyl)methanol 2,6-Dibromoanisole (138.0 g, 0.51 mol) was dissolved in 750 ml of tetrahydrofuran and the solution cooled to -63 C. Butyl lithium (319 ml of 1.6 M, 0.51 mol) was added slowly with stirring and the mixture stirred at -60 C. for 4.5 hours and then 69.4 g (0.51 mol) of o-anisaldehyde in 250 ml of tetrahydrofuran was added slowly with stirring and the mixture allowed to stir cold for 1 hour. The mixture was allowed to warm to ambient temperature and was then poured into a mixture of ice and saturated aqueous ammonium chloride. The resulting mixture was extracted with ether and the ether extract dried over magnesium sulfate and then concentrated by evaporation under reduced pressure to obtain the title compound. This was purified by preparative liquid chromatography eluding with a 5:95 mixture of ethyl acetate and hexane to obtain 44.6 g (24 percent of theory) of material having a proton nmr spectrum consistent with the assigned structure.

The synthetic route of 38603-09-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Dow Chemical Company; US4979978; (1990); A;,
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