Month: May 2021

Reference of 18014-00-1, 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. 18014-00-1, name is Dimethyl 2,5-dibromoterephthalate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 1 Preparation of 2,5-dithien-2-ylterephthalic acid dimethyl ester Dimethyl 2,5-dibromoterephthalate (6.09 g, 17.30 mmol) is dissolved in anhydrous THF (100 cm3), followed by the addition of 2-thienylzinc bromide (0.50 M in THF, 90 cm3, 45.0 mmol) and Pd(PPh3)4 (0.50 g, 0.43 mmol). The mixture is heated at 67 C. for 2 hours. After cooling, the reaction mixture is poured into water. The precipitate is collected by filtration and washed with water, methanol and diethyl ether then dried in vacuo, to yield the product as a pale yellow solid (5.41 g, 87%). 1H NMR (300 MHz, CDCl3): delta(ppm) 7.82 (s, 2H, Ar-H), 7.40 (dd, J=4.8 and 1.4 Hz, 2H, Ar-H), 7.07-7.12 (m, 4H, Ar-H), 3.78 (s, 6H, CH3); 13C NMR (75 MHz, CDCl3): delta(ppm) 168.1 (C=O), 140.3 (q), 133.6 (q), 133.4 (q), 131.9 (CH), 127.5 (CH), 127.0 (CH), 126.7 (CH), 52.6 (CH3); MS (m/e): 358 (M+, 100%), 327, 299, 240, 195.

The synthetic route of Dimethyl 2,5-dibromoterephthalate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GESELLSCHAFT MIT BESCHRANKTER HAFTUNG; US2011/226999; (2011); 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. Safety of Methyl 2-(2-bromophenyl)acetate

General procedure: In a three neck round bottom flask, CaCl2 (1.12 g, 10.2 mmol) was dissolved in ethanol (50 mL) under argon atmosphere. The resulting solution was cooled to 0 ?C, followed by the addition of NaBH4 (0.19 g, 5.1 mmol) at the same temperature. The resulting suspension was allowed to stir at 0 ?C for 30 min, after which a solution of S5a (1.0 g, 3.4 mmol) in 60 mL of Ethanol was added at the same temperature. The resulting reaction mixture was allowed to stir at 0 ?C for another 30 min, and then at rt for 15 h. After 15 h, 50 mL of a mixture of water and dichloromethane (1:1) was added to the reaction mixture which was then sonicated for 1 h. The resulting mixture was then subjected to vacuumfiltration over celite. The filtrate was collected and evaporated under reduced pressure. 50 mL of water was added to the resulting crude, which was then extracted with three portions of dichloromethane (30 mL each). The combined organic layer was dried over Na2SO4, and evaporated under reduced pressure to afford S6 2-(2-bromo-4,5-dimethoxyphenyl)ethanol (S6a): Brown Oil; (2.56 g, 60 %). 2-(2-bromo-5-methoxyphenyl)ethanol (S6b): Clear Oil; (1.29 g, 42 %). 2-(2-bromo-4-methoxyphenyl)ethanol (S6c): Clear Oil; (1.03 g, 55 %). 2-(2-bromophenyl)ethanol (S6d): Clear Oil; (2.41 g, 55 %).

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

Reference:
Article; Kapadia, Nirav; Harding, Wayne; Tetrahedron; vol. 69; 42; (2013); p. 8914 – 8920;,
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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 2967-93-3 as follows. Formula: C9H9FO2

Step 2; Preparation of 2-Fluoro-5-formyl-benzoic acid methyl ester; Add Af-bromosuccinimide (2.46 g, 13.86 mmol) and benzoyl peroxide (0.152 g, 0.630mmol) to a solution of 2-fluoro-5-methyl-benzoic acid methyl ester (1.06 g, 6.30 mmol)in carbon tetrachloride (50 mL). Heat the mixture at reflux for 4 h. Cool the mixture toroom temperature and wash with saturated aqueous sodium bicarbonate solution (10 mL)and brine (10 mL). Dry the organic layer over anhydrous sodium sulfate, filter, andconcentrate under reduced pressure. Dissolve the resulting residue in dimethylsulfoxide(30 mL) and heat at reflux for 16 h. Cool the mixture to room temperature and dilutewith water (100 mL) and ethyl acetate (100 mL). Extract the aqueous layer with ethylacetate (3 x 100 mL). Wash the combined organic layers with water (3 x 100 mL),followed by brine (100 mL). Dry the organic layer over anhydrous sodium sulfate, filterand concentrate. Purify the residue by chromatography over silica gel, eluting withhexanes/ethyl acetate (80:20), to provide the title compound as a tan solid (0.228 g, 20%).

According to the analysis of related databases, 2967-93-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; WO2006/2342; (2006); A1;,
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Electric Literature of 210530-71-5, 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 210530-71-5 as follows.

To a stirred mixture of methyl 2- (3, 4-difluorophenyl) acetate (4.5 g, crude) in CCl4 (50 mL) was added NBS (6.0 g, 33.7 mmol) and HBr/HOAc (1.0 mL) . After the addition, the reaction mixture was stirred for 3 hours at 85. The solid of the reaction was filter out, the filtrate was concentrated, and this residue was dissolved by H2O (50 mL) , extracted with EtOAc (50 mL x 3) , The combined organic layers were washed with brine, dried over Na2SO4, concentrated to give methyl 2-bromo-2- (3, 4-difluorophenyl) acetate (4.0 g, crud) as a yellow oil. MS: M/e 266 (M+1)+

According to the analysis of related databases, 210530-71-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BEIGENE, LTD.; ZHANG, Guoliang; SUN, Hanzi; ZHOU, Changyou; (253 pag.)WO2020/20097; (2020); A1;,
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Application of 167760-75-0,Some common heterocyclic compound, 167760-75-0, name is Methyl 4-amino-3-(trifluoromethyl)benzoate, molecular formula is C9H8F3NO2, 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.

Sodium nitrite (1.21 g, 0.017 mmol) was added to tetrafluoro boric acid (20 mL) in lot wise manner at -10C. The solution was stirred for 1 h at same tempreture then added methyl 4- amino-3-(trifluoromethyl)benzoate (3.5 g, 0.0 15 mmol) and continued stirring for h at sametempreture followed by addition of solution of KI (3.18 g, 0.0 19 mmol) in acetone : water (40 mL:60 mL).The reaction mass was stirred at rt for 1 h. The reaction mass was diluted with water and filtered to afford 4.8 g of title compound. ?H NMR (300 MHz, CDC13): 8.28 (s, 1H), 8.15-8.12 (d, J= 8.1Hz, 1H), 7.84-7.81 (d, J= 8.1Hz, 1H), 3.95(s, 3H).

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-amino-3-(trifluoromethyl)benzoate, its application will become more common.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; MUTHUKAMAN, Nagarajan; PISAL, Dnyandeo; KHAIRATKAR-JOSHI, Neelima; SHAH, Daisy Manish; KADAM, Sheetal R; (303 pag.)WO2016/55947; (2016); A1;,
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1732-08-7, name is Dimethyl pimelate, belongs to esters-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. Quality Control of Dimethyl pimelate

To a 500 ml four-necked flask equipped with a stirring, a thermometer, a reflux condenser, and a constant pressure dropping funnel, 100 g of chloroform, 18.8 g (0.1 mol) of dimethyl 1,7-pimelate, and 0.6 g of 40 wt% were added. Hydrobromic acid, 72.0 g of bromine and 50 g of chloroform were added dropwise at 30-35 C. After the completion of the dropwise addition, the reaction was stirred at 30-35 C for 7 hours, cooled to 20-25 C, and purged with nitrogen for 2 hours. 17 wt% ammonia water, stirring reaction at 60-65 C for 6 hours, then, cooling to 20-25 C, adding 20 g of 30 wt% hydrogen peroxide, stirring at 30-35 C for 4 hours, adding 45 g of 20 wt% aqueous sodium hydroxide solution, The reaction was stirred at 30-35 C for 4 hours, layered, and the organic phase was washed twice with water. Each time 20 g of water, the aqueous phase is combined, the pH of the aqueous phase is adjusted to 2.5-2.0 with hydrochloric acid, filtered, and dried to obtain 15.1 g of a white solid 2,6-pyridinedicarboxylic acid, the liquid phase purity is 99.5%, and the product yield is 90.4%. .

The synthetic route of 1732-08-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xin Fa Pharmaceutical Co., Ltd.; Ju Lizhu; Zhang Mingfeng; Lv Qiangsan; Qi Yuxin; (7 pag.)CN110229096; (2019); A;,
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Application of 179688-27-8,Some common heterocyclic compound, 179688-27-8, name is Ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoate, molecular formula is C15H23NO6, 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 62 N’-[2-Carbethoxy-4,5-bis(2-methoxyethoxy)phenyl]-N,N-dimethylformamidine To a stirred solution of 15.7 g (50 mmol) of ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoate (WO-96130347) in 50 ml of DMF at 0 C. was added phosphorous oxychloride (5.6 ml, 60 mmol) during 15 m. The resulting solution was heated at 55 C. for 45 m, cooled, diluted with methylene chloride, and treated at 0 C. with 200 ml of N/1 sodium hydroxide during 2 m. The organic layer was separated and washed at 0 C. with water. The solution was dried and evaporated with added toluene present to give 18.4 g of amber oil; NMR (CDCl3) delta6 3.02 (s, Me2N).

The synthetic route of 179688-27-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; US6288082; (2001); B1;,
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Application of 35005-25-5, The chemical industry reduces the impact on the environment during synthesis 35005-25-5, name is Isopropyl 3-aminobenzoate, I believe this compound will play a more active role in future production and life.

3-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)propanoic acid (1.0 equiv) and isopropyl 3-aminobenzoate (1.2 equiv) were mixed in DMF, and the resulting mixture was added to HATU (1.5 equiv) and DIPEA (1.5 equiv). The reaction mixture was stirred overnight at room temperature and concentrated under reduced pressure, and the obtained residue was diluted with EtOAc and washed with water and brine. An organic layer was collected and dehydrated with anhydrous MgSO4, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography, thereby obtaining isopropyl 3-(3-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)propanamido)benzoate (transparent liquid, 0.06 g, 26.5% yield). (0364) 1H-NMR (500 MHz, CDCl3) 7.99 (brs, 2H), 7.93 (d, J=7.0 Hz, 1H), 7.79 (d, J=7.0 Hz, 1H), 7.41 (t, J=8.0 Hz, 1H), 7.32 (d, J=9.0 Hz, 2H), 6.89 (d, J=8.0 Hz, 2H), 5.25 (m, 1H), 4.35 (t, J=6.0 Hz, 2H), 2.87 (t, J=6.0 Hz, 2H), 1.72 (s, 2H), 1.38 (d, J=6.5 Hz, 6H), 1.36 (s, 6H), 0.72 (s, 9H); 13C-NMR (125 MHz, CDCl3) delta 169.2, 165.7, 155.6, 143.4, 137.9, 131.6, 129.1, 127.3, 125.3, 124.3, 120.6, 113.8, 68.6, 64.1, 56.9, 38.0, 37.8, 32.3, 31.8, 31.7, 21.9.

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, Isopropyl 3-aminobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DONGGUK UNIVERSITY GYEONGJU CAMPUS INDUSTRY-ACADEMY COOPERATION FOUNDATION; KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY; Lee, Kyeong; Won, Mi Sun; Ban, Hyun Seung; Kim, Minkyoung; Kim, Bo Kyung; (40 pag.)US2020/31764; (2020); 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. 2216-45-7, name is 4-Methylbenzyl acetate, A new synthetic method of this compound is introduced below., SDS of cas: 2216-45-7

General procedure: A mixture of benzonitrile (5 mmol), benzyl acetate (6 mmol),and Fe(ClO4)3·H2O (5 mol%) was placed in a round-bottomedflask. Then, the reaction mixture was heated at 80 C for 5 h.After completion of the reaction monitored by thin layer chromatography(TLC), water (10 mL) was added, and the reactionmixture was extracted with ethyl acetate (3 × 20 mL). Theorganic layers were collected, combined, washed with water(3 × 20 mL), dried with anhydrous Na2SO4, and concentratedunder vacuum. The pure product was obtained by directlypassing through a silica gel (200-300 mesh) column to give awhite powder a (0.91 g, 87% yield)..

The synthetic route of 2216-45-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Feng, Chengliang; Yan, Bin; Yin, Guibo; Chen, Junqing; Ji, Min; Synlett; vol. 29; 17; (2018); p. 2257 – 2264;,
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These common heterocyclic compound, 63243-76-5, name is Ethyl 2-amino-5-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. HPLC of Formula: C9H10BrNO2

[00384] The mixture of 2-amino-5-bromo-benzoic acid ethyl ester (3.0 g, 13.16 mmol) and (0979) cyclopropanecarbonitrile (2.6 g, 39.47 mmol) in 6 M HCl/dioxane (60 mL) was stirred at reflux overnight. The solid was filtered, dried in vacuum to give 6-bromo-2-cyclopropyl-quinazolin-4-ol (3.3 g, yield: 95%) as crude product. MS: m/z 249.1 (M+H+).

The synthetic route of Ethyl 2-amino-5-bromobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HEDRICK Michael P.; HERSHBERGER Paul M.; MALONEY Patrick R.; PEDDIBHOTLA Satyamaheshwar; PINKERTON Anthony B.; WO2015/200534; A2; (2015);,
Ester – Wikipedia,
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