Category: esters-buliding-blocks

Electric Literature of 69038-74-0, These common heterocyclic compound, 69038-74-0, name is tert-Butyl 3-Bromobenzoate, 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.

(+)-Pinanediol 3-(teri-butoxycarbonyl)benzeneboronate (12b). A solution of tert- butyl 3-bromo-benzoate (1.70 g, 6.61 mmol), obtained from 3-bromobenzoic acid, (Wright, S. W. et al, Tetrahedron Lett. 1997, 38, 7345-7348) and freshly distilled triisopropyl borate (1.53 mL, 6.61 mmol) in THF (17 mL) was cooled to -100 °C under argon flow and w-butyllithium (2.5 M soln in hexane, 2.91 mL, 7.27 mmol) was added dropwise over 15 min, during which the solution turned cherry red. After 1 h at -100 °C, trimethylsilyl chloride (0.84 mL, 6.61 mmol) was dropped into the reactor and the resulting colorless solution was allowed to warm to room temperature and stirred overnight. Finally, (+)-pinanediol (1.12 g, 6.61 mmol) was added and the solution stirred 1 h at room temperature. The mixture was partitioned between ethyl acetate (100 mL) and water (40 mL) and the aqueous phase was extracted with ethyl acetate (2 x 50 mL). The combined organic phases were washed with brine, dried over MgS04, filtered and concentrated in vacuo. The crude residue was purified by column chromatography (light petroleum/ethyl ether 95:5), affording 12b as a yellowish solid (2.10 g, 89percent yield). Mp 70-71 °C. [CC]D +7.3 (c 1.1, CHCI3). XH-NMR (400 MHz, CDC13): delta 0.94 (3H, s, pinanyl CH»), 1.24 (1H, d, J 10.9, pinanyl Hendo), 1.36 (3H, s, pinanyl G¾), 1.53 (3H, s, pinanyl CH3), 1.64 (9H, s, f-Bu), 1.98-2.30 (5H, m, pinanyl protons), 4.51 (1H, dd, J 8.5, 2.0, CHOB), 7.46 (1Eta, t, J7.6, ¾), 8.0 (1Eta, d, J 7.6, H4), 8.12 (1H, d, J7.6, H6), 8.45 (1H, s, H2). 13C-NMR (100 MHz, CDCI3): delta 24.0, 26.5, 27.1, 28.2, 28.7, 35.5, 38.2, 39.5, 51.4, 78.4, 80.9, 86.5, 127.6, 131.5, 132.1, 135.7, 138.7, 169.5, CB not seen. EI-MS: m/z 356 (M+, 10percent), 300 (36), 283 (41), 231 (50), 204 (38), 83 (65), 67 (59), 57 (100). Anal. Calcd. for C2iH29B04: C, 70.80; H, 8.20. Found: C, 70.55; H, 8.22.

The synthetic route of 69038-74-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; UNIVERSITA’ DEGLI STUDI DI MODENA E REGGIO EMILIA; SHOICHET, Brian K.; PRATI, Fabio; CASELLI, Emilia; ROMAGNOLI, Chiara; EIDAM, Oliv; WO2013/56163; (2013); 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. 53088-68-9, name is Methyl (3-Chlorophenyl)acetate, A new synthetic method of this compound is introduced below., Formula: C9H9ClO2

REFERENCE EXAMPLE 30 Methyl (RS)-a-bromo-(3-chlorophenyl)acetate A mixture of Reference Example 29 (5.0 g), N-bromosuccinimide (5.3 g) and azobisisobutyronitrile (0.38 g) in dry chloroform (50 ml) was heated at reflux for 6 hours. The reaction mixture was washed four times with water (50 ml) and the organic phase dried over magnesium sulphate and evaporated. The residual oil was purified by flash chromatography on silica eluding with a mixture of ethyl acetate and pentane (5:95, v/v). Fractions homogenous in the required product were combined and evaporated to give the title compound (4.3 g) as an oil.

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; Rhone-Poulenc Rorer Limited; US6048893; (2000); A;; ; Patent; Rhone-Poulenc Rorer Limited; US6124343; (2000); A;,
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Adding a certain compound to certain chemical reactions, such as: 94-46-2, name is Isoamyl Benzoate, belongs to esters-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 94-46-2, Safety of Isoamyl Benzoate

Trifluoromethylthio silver (0.5 mmol), 2,6-lutidine (0.1 mmol) and ammonium persulfate (1.0 mmol) were added to the reaction flask, and after evacuating the argon three times, isoamyl benzoate 1.0 mmol) and acetonitrile (5 mL). The reaction flask was placed in an oil bath at 90 C start heating and stirring 2h removed, to be cooled to room temperature. Using trifluoromethylbenzene as an internal standard substance, it was confirmed by 19F-NMR that 3-methyl-3-trifluoromethylthiobutyl benzoate was formed (a yield of 63%). The reaction mixture was filtered and the filtrate was evaporated to remove the solvent by a rotary evaporator. The residue was separated by column chromatography and concentrated under reduced pressure to give a colorless oil (75 mg, yield 51%).

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; Chinese Academy Of Sciences Shanghai Organic Chemistry Institute; Chen Qingyun; Liu Chao; Wu Hao; Xiao Zhiwei; (15 pag.)CN104557358; (2017); B;,
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Some common heterocyclic compound, 18014-00-1, name is Dimethyl 2,5-dibromoterephthalate, molecular formula is C10H8Br2O4, 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. Computed Properties of C10H8Br2O4

Raw material 1 (11.6 g, 55 mmol) and methyl 2,5-dibromoterephthalate (17.6 g, 50 mmol) were dissolved in 200In ml of toluene, add 50 ml of 2M aqueous sodium carbonate and 50 ml of ethanol.After purging with nitrogen for 30 minutes, catalyst tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 3.5 g, 3.0 mmol) was added and heated to 100C with stirring.After 15 hours of reaction, cooling at room temperature, adding dichloromethane and deionized water, extracting the organic phase and drying over anhydrous magnesium sulfate,After filtration, depressurizing, concentrating, and separation and purification with a silica gel column, about 21.6 g (41 mmol) of pure Intermediate 1 was obtained in a yield of about 82%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 18014-00-1, its application will become more common.

Reference:
Patent; Shanghai Hehui Optoelectric Co., Ltd.; Wang Liping; (15 pag.)CN107573357; (2018); A;,
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Adding a certain compound to certain chemical reactions, such as: 1312610-07-3, name is Ethyl 7-bromobenzo[d][1,3]dioxole-4-carboxylate, belongs to esters-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 1312610-07-3, Formula: C10H9BrO4

To a solution of compound I-IXa (700 mg, 2.6 mmol) in toluene (15.0 mL), EtOH (3.0 mL)Aq. Na2CO3 (2.0 M, 1.5 mL) and 4-(methoxycarbonyl)phenylboronic acid,The mixture was stirred under a nitrogen atmosphere for 10 minutes, then Pd(Ph3P)4 (90 mg, 0.08 mmol) was added and the flask was purged three times with nitrogen.The mixture was stirred at 80 C for 10 hours.After cooling to room temperature, the reaction mixture was extracted with ethyl acetate and washed with water and brine.Solvent removal and purification of the residue on silica gel by column chromatography(eluent: PE: EtOAc = 6:1)Compound I-IXb (560 mg, yield 59%) was obtained as a yellow 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, Ethyl 7-bromobenzo[d][1,3]dioxole-4-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Beijing Kaiyin Technology Co., Ltd.; Xiong Guoyu; Yang Jian; Zhou Desheng; Pan Hai; Yan Fukun; (19 pag.)CN108675998; (2018); 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. 73792-12-8, name is Ethyl 4-amino-3-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 73792-12-8

Step 1 : Ethyl 3-fluoro-4-hydrazinylbenzoate hydrochloride: To a stirred and cooled (-20C) solution of ethyl 4-amino-3-fluorobenzoate (18 g, 98.809 mmol) in cone. HC1 (200 mL) was added aqueous solution of NaN02 (7.5 g, 108.69 mmol). This mixture was added very slowly to a precooled (-10 C) mixture of and tin chloride (100 g, 444.7 mmol) in cone. HC1 (80 mL) and stirred at the same temperature for 30 min. The precipitate obtained was filtered and washed with diethyl ether (2 x 100 mL) to obtain 19.6 g of the title compound as white solid. 1H NMR (300 MHz, DMSO-i) delta 1.30 (t, J = 7.2 Hz, 3H), 4.27 (q, J = 6.9 Hz, 2H), 7.19 (t, J = 8.1 Hz, 1H), 7.67 (d, J = 8.1 Hz, 1H), 7.78 (d, J = 8.4 Hz, 1H), 8.94 (br s, 1H), 10.50 (br s, 2H); APCI-MS (m/z) 199 (M+H)+.

According to the analysis of related databases, 73792-12-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; DAS, Sanjib; CHAUDHARI, Sachin Sundarlal; THOMAS, Abraham; PARDESHI, Shailesh Ramesh; DESHMUKH, Vishal Govindrao; WADEKAR, Prashant Dilip; KHAIRATKAR-JOSHI, Neelima; SHAH, Daisy Manish; BAJPAI, Malini; WO2015/87234; (2015); A1;,
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Electric Literature of 651734-58-6,Some common heterocyclic compound, 651734-58-6, name is Methyl 2-fluoro-3,5-dimethoxybenzoate, molecular formula is C10H11FO4, 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.

b. methyl 2-chloro-6-fluoro-3,5-dimethoxybenzoate S02C12 (2.20g, 0.016mol) was added dropwise to a solution of methyI-2-fluoro-3,5-dimethoxy benzoate (3.5g, 0.016 mol) in acetonitrile (40mL) at 0C under nitrogen atmosphere. The resulting reaction mixture was warmed to room temperature slowly and stirred for lh. The reaction mixture was quenched with saturated sodium bicarbonate solution, and extracted with ethyl acetate (3x30mL). The organic phase was washed with brine, dried over Na2S0 , filtered, and concentrated. The residue was purified by silica gel column chromatography using eluent (gradient hexane/ether (20:1) to hexane/ether (5:1) to afford the title compound (2.7g, yield: 67%) as a solid.

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-fluoro-3,5-dimethoxybenzoate, its application will become more common.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; REYNOLDS, Dominic; HAO, Ming-Hong; WANG, John; PRAJAPATI, Sudeep; SATOH, Takashi; SELVARAJ, Anand; WO2015/57938; (2015); A1;,
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Synthetic Route of 144267-97-0, 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 144267-97-0 as follows.

5-Fluoro-6-[5-(benzyloxy)benzifnid zol-l-yl]-l,3-dihvdro-l-hydwxy-2,l- benzoxaborole Preparation of ethyl 2-bromo-5-fluoro-4-(4-methoxy-2-nitrophenylamino) benzoate[0242] To a solution of 4-methoxy-2-nitroaniline (6 g, 22.6 mmol, 1 eq) and ethyl 2-bromo-4,5-difluorobenzoate (3.8 g, 22.6 mmol, 1 eq) in dry DMF (225 mL) was added CS2CO3 (12.7 g, 33.9 mmol, 1.5 eq) under N2 protection. The mixture was heated to 100C for 4h. TLC analysis showed there was no starting material remained. The mixture was mixed with 300mL water. The mixture was extracted with EA (2 x 100 mL) and the organic layer separated was washed with 0.5N HCl, water, brine and dried over anhydrous Na2S04. The mixture was filtered and the filtrate was concentrated. The solid was purified by recrystallization with EA/PE to give 6 g of product (yield 65%).

According to the analysis of related databases, 144267-97-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; ZHANG, Yong-kang; ZHOU, Huchen; DING, Charles; PLATTNER, Jacob, J.; FREUND, Yvonne; WO2011/63293; (2011); A1;,
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Related Products of 29006-01-7,Some common heterocyclic compound, 29006-01-7, name is Methyl 4-methoxybutanoate, molecular formula is C6H12O3, 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.

Lithium diisopropylamide was prepared by addition of n-butyllithium (2.5 M in hexanes, 11.7 mL, 58.8 mmol) to diisopropylamine (9.7 mL, 70.6 mmol) in dry tetrahydrofuran (100 mL) at -78 C. Stirring was continued for 15 min at -78 C before methyl 4-methoxybutanoate (6.84 g, 51.8 mmol) was added to the reaction mixture. Stirring was continued for 20 min at -78C and benzaldehyde (5g, 47.1 mmol) in tetrahydrofuran (20 mL) was added, and the reaction mixture allowed to warm slowly to room temperature. Stirring was continued for 2 hours, water (50 mL) was added under stirring and the mixture was extracted with ether (3 x 50 mL). The combined organic extracts were washed with brine, dried with sodium sulfate, filtered and evaporated under reduced pressure to afford methyl 2-(hydroxy(phenyl)methyl)-4-methoxybutanoate (10.7 g, 44.9 mmol) in 95% yield. LCMS (ESI+): 261.1 (M+Na).

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

Reference:
Patent; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; AUDIA, James, Edmund; COTE, Alexandre; DUPLESSIS, Martin; GEHLING, Victor, S.; HARMANGE, Jean-christophe; VASWANI, Rishi, G.; (274 pag.)WO2016/172496; (2016); 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. 111-79-5, name is Methyl non-2-enoate, A new synthetic method of this compound is introduced below., Recommanded Product: 111-79-5

PREPARATION 2 4-Nitro-beta-hexyl-1H-imidazole-1-propanoic acid methyl ester The title intermediate was prepared by combining 5.0 grams of 4-nitroimidazole, 8.26 g of methyl 2-nonenate, 4.08 g of sodium bicarbonate, and 200 ml of dimethylformamide and heating the mixture at 80 C. for 18 hours. After cooling, the mixture was poured into water and extracted into ethyl acetate. The organic layer was concentrated in vacuo and the residue purified by HPLC over a silica column eluding with ethyl acetate. The appropriate fractions were combined and concentrated in vacuo to provide 2.2 g of the desired titled intermediate. Analysis for C13 H21 N3 O4: Calc.: C, 55.11; H, 7.47; N, 14.83; Found: C, 55.37; H, 7.37; N, 14.58.

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; Eli Lilly and Company; US5073566; (1991); A;,
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Ester – an overview | ScienceDirect Topics