Month: May 2021

Electric Literature of 260806-90-4, 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. 260806-90-4 name is Methyl 3-bromo-2-methoxybenzoate, 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 methyl-3-bromo-2-methoxylbenzoate 6 (1.5 g, 6.12 mmol) in 13 mL of anhydrous 1,4-dioxane were subsequently added bis(pinacolate)diboron (2.3 g, 9.18 mmol), potassium acetate (1.5 g, 15.3 mmol), followed by bis(diphenylphospinoferrocene)palladium dichloride (134.6 mg, 0.184 mmol). The resulting mixture was heated to 110 C in an oil bath for 2 h or to 130 C in a microwave reactor for 30 min (5 bar, 200 W). Afterwards, the solvent was removed under reduced pressure to afford the crude pinacol ester that was used in the following step without further purification. Then, ammonium acetate (1.4 g, 18.36 mmol) and sodium periodate (3.9 g, 18.36 mmol) were added to a solution of the crude pinacol ester in a mixed solution of acetone (11.0 mL) and water (11.0 mL). The resulting mixture was stirred at r.t. until complete conversion of the starting material was observed by TLC. The precipitate was then filtered off, and the filtrate was concentrated under reduce pressure. The residue was extracted with ethyl acetate, and the combined organic extracts were dried over anhydrous Na2SO4, filtered and evaporated. The crude product was finally purified by silica gel column chromatography (n-hexane/ethyl acetate 6:4) to give 2-methoxy-3-(methoxycarbonyl)phenylboronic acid 7 (938.6 mg, 4.47 mmol). Yield: 73%. 1H NMR (400 MHz, CDCl3) delta (ppm): 8.04 (dd, 1H, J = 7.4 Hz, J = 1.9 Hz, H4), 7.96 (dd, 1H, J = 7.8 Hz, J = 1.9 Hz, H6), 7.24 (t, 1H, J = 7.5 Hz, H5), 6.15 (bs, 2H, B(OH)2), 3.94 (s, 3H, OCH3), 3.92 (s, 3H, COOCH3).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-bromo-2-methoxybenzoate, and friends who are interested can also refer to it.

Reference:
Article; Bertini, Simone; Chicca, Andrea; Arena, Chiara; Chicca, Stefano; Saccomanni, Giuseppe; Gertsch, Juerg; Manera, Clementina; Macchia, Marco; European Journal of Medicinal Chemistry; vol. 116; (2016); p. 252 – 266;,
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Related Products of 87808-49-9,Some common heterocyclic compound, 87808-49-9, name is Methyl 2-bromo-4-methylbenzoate, molecular formula is C9H9BrO2, 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 1: Preparation of 3-(2-bromo-4-methylphenyl)pentan-3-ol To a solution of methyl 2-bromo-4-methylbenzoate (10 g, 43.7 mmol) in THF (10 mL) was added dropwise EtMgBr (88 mL, 262 mmol) at 0 C. under nitrogen and then stirred at rt for 12 h. The reaction mixture was quenched with NH4Cl-saturated water and extracted with EA. The combined organic layer was washed with NaHCO3 solution and brine, dried over Na2SO4. The solution was concentrated and the residue was purified by column chromatography over silica gel eluted with PE-EA (10:1?2:1) to provide 3-(2-bromo-4-methylphenyl)pentan-3-ol (8.09 g; yield 71.2%) as a white solid. 1H NMR (400 MHz, CDCl3): delta 7.67 (d, 1H), 7.52 (s, 1H), 7.23 (d, 1H), 2.35 (s, 3H), 1.83 (m, 4H), 0.77 (t, 6H) ppm.

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

Reference:
Patent; Anacor Pharmaceuticals, Inc.; Eli Lilly and Company; AKAMA, Tsutomu; Balko, Terry William; Defauw, Jean Marie; Plattner, Jacob J.; White, William Hunter; Winkle, Joseph Raymond; Zhang, Yong-Kang; Zhou, Yasheen; US2013/131017; (2013); 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. 25081-39-4, name is Methyl 3,5-dimethylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 25081-39-4

(iii) Methyl-3,5-bis(bromometylene)benzoate (5) The ester (4, 2.76 g, 0.0168 mol), N-bromosuccinimide (6.07 g, 0.0341 mol) and benzoyl peroxide (85 mg, 0.35 mmol) were placed in 100 ml round-bottom flask. Then dried carbon tetrachloride (25 ml) was added and heated under the reflux conditions for 3 h. After cooling to room temperature, the mixture was filtered and the solvent was evaporated in vacuo to obtain the crude product as residue (5.39 g). The crude product was crystallized from hexane to yield the dibromide (5): 1.37 g (25%), mp. 94-98 C. 1H NMR (300 MHz, CDCl3) delta: 8.00 (s, 2H, arom. H); 7.61 (s, 1H, arom. H); 4.50 (s, 4H, CH2Br); 3.93 ppm (s, 3H, COOCH3).

The synthetic route of 25081-39-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Przyby?, Bartosz; Zo?, Jerzy; Janczak, Jan; Journal of Molecular Structure; vol. 1048; (2013); p. 172 – 178;,
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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. 31273-66-2, name is Ethyl 2,3-dichlorobenzoate, A new synthetic method of this compound is introduced below., name: Ethyl 2,3-dichlorobenzoate

General procedure: In a fume hood, an oven dried Schlenk flask equipped with a magnetic stirring bar was filled with N2 and evacuated (three cycles). Under N2 atmosphere [Ir(OMe)(COD)]2 (13.3 mg, 0.01 mmol, 1 mol%), 4,4-ditert-butyl-2,2?-bipyridyl (10.7 mg, 0.02 mmol, 2 mol%), and pinacolborane (HBPin) (436 muL, 384 mg, 3 mmol, 1.5 equiv) were added. The appropriate arene substrate (2 mmol, 1 equiv) was added via micropipette under N2 atmosphere. The Schlenk flask was closed and the reaction mixture was heated at 80 C in an oil bath. The progress of reaction was monitored by GC-MS and TLC. Upon completion of reaction, Schlenk flask was cooled to r.t. and exposed to air. The contents of the flask were dissolved in CH2Cl2 (3-5 mL) and taken out in a round-bottomed flask. The volatile organics were removed under reduced pressure using a rotary evaporator. The crude product was purified by column chromatography (silica gel, hexanes-CH2Cl2 1:1).

The synthetic route of 31273-66-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shahzadi, Tayyaba; Saleem, Rahman S. Z.; Chotana, Ghayoor A.; Synthesis; vol. 50; 21; (2018); p. 4336 – 4342;,
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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 6942-39-8 as follows. Recommanded Product: Methyl 2-bromo-5-fluorobenzoate

Example 16a) 2-Bromo-5-dimethylamino-benzoic acid methyl ester (16a)To a stirred solution of 5,24 g (22.5 mmol) 2-Bromo-5-fluoro-benzoic acid methyl ester (Rarechemicals) and 60.0 ml dimethylsulphoxid were added 2.23 g (27.0 mmol) dimethylamine hydrochloride and 6.54 g (47.3 mmol) potassium carbonate. The reaction mixture was stirred for 11 h at 7O0C in an autoclave and was concentrated with high vacuum rotation evaporator at 650C. The residue was diluted with dichloromethane, washed twice with water. The combined water phases were extracted with dichloromethane. The combined dichloromethane phases were washed with diluted sodium hydrogen carbonate solution, dried with sodium sulphate and concentrated. The oily crude was purified by column chromatography and the desired product 16a was obtained in 70 % yield (4,08 g, 15.8 mmol).MS-ESI: 258/560 (M+ +1 , 90/81).Elementary analysis: C 46.53% H 4.69% N 5.43%Determined: C 46,59% H 4.72% N 5.41%

According to the analysis of related databases, 6942-39-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; WO2008/28688; (2008); A2;,
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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. 869-10-3, name is Diethyl 2,5-dibromohexanedioate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Diethyl 2,5-dibromohexanedioate

A solution of diethyl 2,5-dibromoadipic acid (8.0 g, 0.0222 mol) in toluene (25 mL) was heated to 80C and after stopping the heating, thereto was added dropwise 2-methoxyaniline (4.1 g, 0.333 mol) over 40 min., and the mixture was stirred at 100C for 11 hours again. The reaction solution was filtered under reduced pressure and the filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography to give the title compound 2.08 g as white solids. 1H-NMR (CDCl3) delta; 1.25 (6H, t, J=7.2Hz), 2.21 (4H, m), 3.71 (3H, s), 4.21 (4H, m), 4.36 (2H, m), 6.70 (1H, m), 6.82 (3H, m).

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 869-10-3.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; EP1736467; (2006); 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. 681128-38-1, name is Ethyl 3,3-difluorocyclobutanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H10F2O2

Preparation 32: 4-(3-chloro-5-(3,3-difluorocyclobutyl)-4,5-dihydro-1H-pyrazol-1-yl)- 2-methylbenzonitrile; Step 1 : ethyl S-O.S-difluorocvclobutvDacrylate; To a solution of ethyl 3,3-difluorocyclobutanecarboxylate (1.94 g, 11.82 mmol) in dichloromethane (40 ml_) at -78C was added diisobutyl aluminum hydride (13 ml_ of a 1.0M solution in hexanes, 13.0 mmol). The reaction was stirred at -78C for 45 min. Saturated aqueous ammonium chloride (40 ml_) was added, and the resulting mixture stirred overnight at room temperature. The biphasic mixture was filtered through celite. The organic layer was dried over sodium sulfate, filtered and concentrated to give 3,3- difluorocyclobutanecarboxaldehyde which was used immediately without further purification. To a suspension of sodium hydride, 60 wt% dispersion in mineral oil (487 mg, 12 mmol) in tetrahydrofuran at 0C was added triethyl phosphonoacetate (2.4 mL, 12.0 mmol) dropwise. After addition was complete, the mixture was allowed to warm to room temperature, and stirred until the suspension cleared (~10 min.). 3,3- difluorocyclobutanecarboxaldehyde was added as a solution in tetrahydrofuran (10 mL). The resulting solution was stirred at room temperature 4 h. Diethyl ether (40 mL) was added, and the reaction was quenched by addition of saturated aqueous ammonium chloride (20 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated. The crude residue was purified by silica gel chromatography eluting with a gradient of 0%-5% ethyl acetate in heptane to yield ethyl 3-(3,3- difluorocyclobutyl)acrylate (498 mg, 22%) as a yellow oil. 1 H NMR ( 400 MHz,CHLOROFORM-d) delta ppm 1.30 (3 H, t, J=7.1 Hz), 2.49 (2 H, m), 2.83 (2 H, m), 2.94 (1 H, m), 4.21 (1 H, q, J=7.2 Hz), 5.85 (1 H, dd, J=15.5, 1.3 Hz), 7.00 (1 H, dd, J=15.5, 7.3 Hz).

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 681128-38-1.

Reference:
Patent; PFIZER INC.; ARHANCET, Graciela Barbieri; CASIMIRO-GARCIA, Agustin; CHEN, Xiangyang; HEPWORTH, David; MEYERS, Marvin Jay; PIOTROWSKI, David Walter; RAHEJA, Raj Kumar; WO2010/116282; (2010); A1;,
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These common heterocyclic compound, 57486-69-8, name is Methyl 2-(2-bromophenyl)acetate, 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 Methyl 2-(2-bromophenyl)acetate

2-(2-Bromophenyl)-propionic acid methyl ester:[0275] In a 500 mL round bottom flask, 5.1460g (45.8603 mmol, 2.2 eq) of the potassium t-butoxide was suspended in 190 mL of clean, dry THF under N2 atmosphere. To this was added 4.7751 g (20.8456 mmol, 1.0 eq) of the methyl ester dissolved in 10 mL of THF. The solution immediately became a cloudy yellow. The reaction solution was allowed to stir for thirty minutes at room temperature. To the stirred reaction was then added 2.86 mL (48.8603 mmol, 2.2 eq) of the methyl iodide in one portion. The reaction was allowed to stir overnight at room temperature. The following morning, the reaction was diluted with 200 mL of H20. The layers were separated and the aqueous solution was extracted with EtOAc (2 x 100 mL). The organic layers were combined, washed with brine (1 x 100 mL) and dried overNa2S04. The solvent was removed under reduced pressure, yielding a deep yellow oil. The oil was taken up in EtOAc and concentrated onto Celite. The product was then purified using silica gel column chromatography, eluting a gradient of 100% heptane to 50% EtOAc in heptane. A colorless oil was isolated. LCMS (m/e): 244 (M+H); NMR (400 MHz, acetone- d6) delta ppm 1.44 (d, J=7.17 Hz, 3 H) 3.50 – 3.72 (m, 3 H) 4.20 (q, J=7.18 Hz, 1 H) 7.11 – 7.26 (m, 1 H) 7.37 (d, J=4.73 Hz, 2 H) 7.56 – 7.66 (m, 1 H).

The synthetic route of Methyl 2-(2-bromophenyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; JACOBS, Robert, T.; CHEN, Daitao; ORR, Matthew; PLATTNER, Jacob, J.; WO2011/116348; (2011); A1;,
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Application of 2672-58-4,Some common heterocyclic compound, 2672-58-4, name is Trimethyl benzene-1,3,5-tricarboxylate, molecular formula is C12H12O6, 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.

Take 8.00 g of trimesic acid methyl ester 35 oC dissolved in 80 mL of anhydrous tetrahydrofuran,Under nitrogen protection by a constant pressure funnel was slowly added dropwise to 3.00 g of lithium aluminum hydride and 300 mL of anhydrous tetrahydrofuran mixture,The dropwise addition was carried out in ice-salt bath, and the temperature was restored to room temperature after the addition was completed. The mixture was stirred at reflux for 70 oC for 24 h,The reaction was carried out under magnetically stirred ice bath-reflux integrated nitrogen protection. After the reaction, the reaction was quenched with about 100 mL of distilled water, the mixture was suction filtered, the filter cake was washed three times with 100 mL of methanol, and the filtrate was distilled under reduced pressure ,80 oC vacuum drying, 5.12 g are tribenzyl alcohol(96% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Trimethyl benzene-1,3,5-tricarboxylate, its application will become more common.

Reference:
Patent; Jilin Chemical College; Gao Wenxiu; Wang Jisi; Lou Dawei; Yu Dandan; Zhang Zhihui; Zhang Hao; (9 pag.)CN107501043; (2017); A;,
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Related Products of 14920-81-1, 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. 14920-81-1 name is Methyl 2,6-dimethylbenzoate, 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.

EXAMPLE 2; Methyl 2-bromomethyl-6-methyl-benzoate; To a solution of methyl 2,6-dimethyl-benzoate (22.0 g, 134 mmol, example 1) in CCl4 (250 mL) is added N-bromo-succinimide (19 g, 107 mmol) followed by benzoyl peroxide (1.0 g, 4.0 p mmol). The resulting solution is warmed to reflux and stirred at this temperature for 20 min. The reaction mixture is then allowed to cool before being diluted with ether (200 mL), filtered and concentrated. The residue is purified by flash chromatography (silica, 4% acetone in hexanes) to give the title compound. This product (approx. 85% purity, remainder is methyl 2,6dimethyl benzoate) is used without further purification. MS (EI) 242, 244 (M+, Br pattern).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2,6-dimethylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; Aventis Pharma Deutschland GmbH; US7005440; (2006); B1;,
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