Category: ethers-buliding-blocks

Electric Literature of 17715-70-7,Some common heterocyclic compound, 17715-70-7, name is 2,4-Dimethoxy-1-fluorobenzene, molecular formula is C8H9FO2, 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.

Preparation 29 6-Fluoro-7-hydroxychroman-4-one A mixture of 1,3-dimethoxybenzene (3.80 mL, 29.0 mmol) and N-fluorodibenzenesulfonamide (4.21 g, 29.21 mmol) was heated at 60 C. overnight. The mixture was cooled and flash chromatographed on silica gel (2*5 inches packed in hexane) with elution proceeding as follows: 3% ethyl acetate/hexane (1000 mL), discarded forerun; 3% ethyl acetate/hexane (1000 mL), 2.69 g of a 2:1 mixture of 2,4-dimethoxyfluorobenzene and starting material which was carried directly into the next step. The product of the above reaction was combined with acetic acid (11 mL) and 48% HBr (11 mL) and refluxed 3 h. The reaction was concentrated and flash chromatographed on silica gel (2*5 inches packed in hexane) with elution proceeding as follows: 10% ethyl acetate/hexane (2000 mL), 0.95 g (43%) of 2,4-dihydroxyfluorobenzene as a waxy white solid which was used without purification. A mixture of 2,4-dihydroxyfluorobenzene (0.15 g, 1.17 mmol), 3-chloropropionic acid (0.13 g, 1.20 mmol) and trifluoromethanesulfonic acid (1 mL) were heated to 80 C. for 3 h. The reaction was poured into water and extracted with ether (3*). The combined organic phase was washed with water and brine, dried over magnesium sulfate, and concentrated to give 2,4-dihydroxy-5-fluoro-beta-chloropropiophenone as a red solid which had: NMR delta 7.37 (d, J=10.8 Hz, 1 H), 6.54 (d, J=7.7 Hz, 1 H), 3.87 (t, J=6.8 Hz, 2 H) 3.33 (t, J=6.8 Hz, 2 H). This product still contained some residual 3-chloropropionic acid but was suitable for use in the next reaction.

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

Reference:
Patent; Pfizer Inc.; US6046213; (2000); A;,
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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 17715-70-7 as follows. category: ethers-buliding-blocks

Example 15 Preparation of 4-fluororesorcinol (15) Using general method E, Compound 11 (27.4 g, 157.9 mmol) gives Compound 15 as 20.7 g (100%) of a colorless crystalline solid: m.p. 94-96 C.; 1 H-NMR (d6 -DMSO) 8.39 (br, 1H), 8.00 (br, 1H), 6.89 (dd, 1H), 6.48 (dd, 1H), 6.27 (ddd, 1H). 19 F-NMR (d6 -DMSO) 145.82 (m). Anal calc. for C6 H5 FO2: C, 56.26; H, 3.93. Found: C, 56.23; H, 3.93.

According to the analysis of related databases, 17715-70-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Molecular Probes, Inc.; US6162931; (2000); A;,
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Related Products of 887267-47-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 887267-47-2 name is 2-Bromo-5-(trifluoromethoxy)aniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a solution of 2-bromo-5-(trifluoromethoxy)aniline (1.00 g, 3.91 mmol, 1.0 eq) in DCM (10 mL) was added TEA (800.0 mg, 7.91 mmol, 1.10 mL, 2.02 eq) and acetyl chloride (620.0 mg, 7.90 mmol, 563.6 muL, 2.02 eq) at 0 C. After 5 h at 0 C, the mixture was warmed to 40 C and stirred for another 7 h under N2. The reaction mixture was poured into H2O (150 mL), and extracted with EtOAc (50 mL*3). The combined organic layers were washed with brine (80 mL), dried over anhydrous Na2SO4, filtered and the filtrate was concentrated in vacuum. The residue was purified by column chromatography (SiO2) to give compound 06-59-1 (900.0 mg, 2.33 mmol, 60% yield). M+H+ = 297.0 (LCMS).1H NMR (CDCl3, 400 MHz): delta 8.41 (br s, 1H), 7.55 (d, J = 8.8 Hz, 1H), 6.88 (dd, J = 1.8, 8.8 Hz, 1H), 2.27 (s, 3H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-5-(trifluoromethoxy)aniline, and friends who are interested can also refer to it.

Reference:
Patent; KYRAS THERAPEUTICS, INC.; VACCA, Joseph P.; LI, Dansu; (587 pag.)WO2017/96045; (2017); A1;,
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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. 53903-49-4, name is 4-Methoxy-2-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., Formula: C8H8F3NO

2-Amino-5-methoxy-benzotrifluoride (10.46 mmol), K3PO4 (15.7 mmol), Xphos (1.05 mmol) and Pd4(dba)3 (0.314 mmol) were added under nitrogen to a solution of 4-bromo-2-fluoro-benzonitrile (10.46 mmol) in 50 mL toluene and the mixture was stirred for 20 hours at a bath temperature of 110 C. Then the mixture was filtered through a glass fibre filter, then the filtrate was extracted with 150 mL water. The organic phase was dried on sodium sulphate and evaporated down. In this way the product was obtained in a yield of 87% of theory. C15H10F4N2O (310.2) Mass spectrum (ESI): [M+H]+=311 [M-H]-=309 Thin layer chromatograph (silica gel; petroleum ether/ethyl acetate 7:3): Rf=0.48

The synthetic route of 53903-49-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/208823; (2012); A1;,
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Application of 92028-21-2,Some common heterocyclic compound, 92028-21-2, name is 6-Methoxy-[1,1′-biphenyl]-3-amine hydrochloride, molecular formula is C13H14ClNO, 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 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)-11beta-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.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Methoxy-[1,1′-biphenyl]-3-amine hydrochloride, its application will become more common.

Reference:
Patent; Moran, Edmund J.; Jacobsen, John R.; Leadbetter, Michael R.; Nodwell, Matthew B.; Trapp, Sean G.; Aggen, James; Church, Timothy J.; US2003/229058; (2003); A1;,
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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. name: 4-Bromo-1-(dimethoxymethyl)-2-fluorobenzene

4-Bromo-1-(dimethoxymethyl)-2-fluorobenzene (87.0 g, 349.27 mmol) was dissolved in THF (700 mL) and cooled to -78 C. n-Butyl lithium (185.42 mL of a 2.5 M soln in hexanes, 461.04 mmol) was rapidly added and immediately followed by addition of DMF (40.40 mL, 523.91 mmol). Reaction was stirred in the cold for 30 min then allowed to warm to rt and stirred for 1 h. The reaction solution was diluted with H2O (500 mL) and extracted with Et2O (3*500 mL). The combined organic extracts were washed with brine (3*200 mL), dried (Na2SO4), filtered, concentrated and chromatographed (eluted with 10% EtOAc in hexanes) to provide 45.90 g of 4-(dimethoxymethyl)-3-fluorobenzaldehyde as a clear oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 439814-87-6, its application will become more common.

Reference:
Patent; Pfizer Inc; US2006/58361; (2006); A1;,
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Related Products of 202865-58-5,Some common heterocyclic compound, 202865-58-5, name is 1-Bromo-4,5-difluoro-2-methoxybenzene, molecular formula is C7H5BrF2O, 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.

1-bromo-4,5-difluoro-2-Methoxy – benzene (1.0g, 4.5mml), 4- (4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl) phenol (1.09g, 4.93mmol), PdCl2 (dppf) (328mg, 0.448mmol) and sodium carbonate (1.51g, 11.2mmol) of 1,4-dioxane and a mixed solution of water (40mL, v / v = 4/1) in addition, at 100 the mixture was stirred for 1 hour. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, and dried with anhydrous magnesium sulfate. After the solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel chromatography (hexane / ethyl acetate), to give the title compound. Yield: 1.13g (3.56mmol) Yield: 79%

The synthetic route of 202865-58-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AJINOMOTO COMPANY INCORPORATED; MIYANAGA, WATARU; NAKAGAWA, TADAKIYO; DOHI, MIZUKI; MATSUMOTO, KAYO; TOKUMASU, MUNETAKA; TAKESHITA, SEN; (58 pag.)JP2016/13983; (2016); A;,
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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. 35202-55-2, name is (3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methanamine hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., category: ethers-buliding-blocks

1.5 mL of ethyl chloroformate are poured into a suspension of 3.4 g of the compound obtained in Step 1 in 4.5 mL of triethylamine and 50 mL of dichloromethane and left overnight, whilst stiffing at ambient temperature; washing with water and with 1N hydrochloric acid is then carried out. Drying is carried out and the solvent is evaporated off to dryness. 3.2 g of an oil corresponding to the expected product are obtained. [0046] Yield=80%

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 35202-55-2.

Reference:
Patent; LES LABORATOIRES SERVIER; CARRANZA, Maria Del Pilar; GARCIA ARANDA, Maria Isabel; GONZALEZ, Jose Lorenzo; SANCHEZ, Frederic; US2014/163220; (2014); A1;,
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Electric Literature of 4132-48-3, 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. 4132-48-3, name is 4-Isopropylanisole, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 4 To each of two-separate 22-L three-necked, round-bottomed reaction flasks equally equipped with thermometer, reflux condenser and mechanical stirrer, there were charged 1.3 Kg (7.4 moles) of 4-isopropylanisole (the product of Example 2) and 12.0 L of trifluoroacetic acid at ambient temperatures (ca. 20 C.) with constant agitation being maintained throughout the course of the entire addition step. This was then followed by the slow addition of 1.0 Kg (7.4 moles) of hexamethylenetetramine in small portions over a 50-minute period to the two well-stirred reaction mixtures now contained in each of the two-separate reaction flasks. The resulting reaction mixture in each flask then exothermed from 24 C. to 38 C. in each instance and was thereafter externally heated up to the reflux temperature of the reaction mixture at 81 C. The stirred and heated reaction mixture was next refluxed at this point for a period of 14 hours. Upon completion of this step, the trifluoroacetic acid solvent was removed from each of the two spent reaction mixtures via concentration under reduced pressure and each resulting residual oil was thereafter partitioned between 4 L of water and 4 L of hexanes. The pH of the two-phase system now contained in each flask was subsequently re-adjusted from a pH value of 0.5 to a value of pH 9.0 by adding thereto separate-3.8 L and 4.2 L portions of 6N aqueous sodium hydroxide solution, respectively. The basified two-phase systems were then allowed to settle and separate, and the two-separated aqueous layers were thereafter saved and subsequently washed with a fresh 2 L-portion of hexanes. The organic layers were next combined and subsequently backwashed with 3 L of water, followed by treatment with 200 g of activated charcoal and 400 g of anhydrous magnesium sulfate as drying agent. After removal of the latter two substances by means of suction filtration through celite, the resulting clear organic filtrate was subsequently concentrated in vacuo to give 2.0 Kg (72%) of crude aldehyde final product in the form of a dark residual oil. The latter material (1.8 Kg) was then purified by means of distillation in vacuo to ultimately afford 880 g (44%) of pure 2-methoxy-5-isopropylbenzaldehyde. The pure product was characterized by means of nuclear magnetic resonance (NMR) data. NMR Data: 1 H NMR(CD3 OD) delta1.05(d, 6H), 2.74(m, 1H), 3.75(s, 3H), 6.95(d, 1H), 7.35(dd, 1H), 7.35(dd, 1H), 7.5 1H, 10.23(s, 1H).

The chemical industry reduces the impact on the environment during synthesis 4-Isopropylanisole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Pfizer Inc.; US5294744; (1994); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 6850-60-8,Some common heterocyclic compound, 6850-60-8, name is (4-Ethoxyphenyl)methanamine, molecular formula is C9H13NO, 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 corresponding primary amine (1.1 equiv.) and an excess of 37% formalinaldehyde free of paraformaldehyde (1.0 mL, 13.5 mmol) were added to a suspension of Guareschi imide triethylammonium salt 1a-c (0.8-0.9 mmol) in EtOH (6-12 mL). The mixture was refluxed for 3-5 min with stirring and allowed to stand for48 h at 20 C (precipitation of the corresponding “bispidinate”5a-m is possible). The mixture was acidified with 10% aqueousHCl to pH 3-4, after 1 day a precipitate formed was collected by filtration, washed with cold EtOH and diethyl ether, and, if necessary, recrystallized from the acetone-EtOH solvent system

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

Reference:
Article; Chigorina; Frolov; Dotsenko; Goloveshkin; Bushmarinov; Krivokolysko; Russian Chemical Bulletin; vol. 65; 9; (2016); p. 2260 – 2269; Izv. Akad. Nauk, Ser. Khim.; 9; (2016); p. 2260 – 2269,10;,
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