Month: June 2021

Synthetic Route of 383-62-0, The chemical industry reduces the impact on the environment during synthesis 383-62-0, name is Ethyl 2-chloro-2,2-difluoroacetate, I believe this compound will play a more active role in future production and life.

EXAMPLE 12 2,3′-Dichloro-2,2-difluoroacetophenone A solution of 25 g of 3-bromochlorobenzene in 100 ml ether was added to a solution of 15.1 g of tetramethylenediamine, 52.4 ml of a 2.5M solution of n-butyllithium in hexane and 75 ml ether at -78 C. under nitrogen. After 1 hour, a solution of 31.0 g of ethyl chlorodifluoroacetate in 150 ml ether was added. After warming to room temperature, the reaction was poured into excess ammonium chloride solution and extracted with ether. The extracts were dried (Na2 SO4) and evaporated. The residue was distilled (0.1 mm Hg) to give 14.7 g of an oil which was used directly.

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 2-chloro-2,2-difluoroacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hoechst-Roussel Pharmaceuticals Inc.; US5006563; (1991); A;,
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Electric Literature of 139102-34-4, 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. 139102-34-4 name is Methyl 4-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.

Under the protection of nitrogen,Compound 46C (232 mg, 1 mmol),Methyl 4-bromo-2-methoxybenzoate (257 mg, 1.05 mmol),Palladium acetate (22.5 mg, 0.1 mmol), BINAP (62.5 mg, 0.1 mmol),The 1,4-dioxane solution of cesium carbonate (489 mg, 1.5 mmol) was heated to 110 C for 4 hours, then cooled to room temperature, quenched with aqueous solution, filtered, and extracted with ethyl acetate.Dry with anhydrous sodium sulfate,The compound was quenched under reduced pressure to give compound 46D (158 mg, 40% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-bromo-2-methoxybenzoate, and friends who are interested can also refer to it.

Reference:
Patent; Jiangsu Xiansheng Pharmaceutical Co., Ltd.; Chen Huanming; Liang Bo; Cao Wenjie; Zhang Guiping; Zhao Zhongqiang; Jiang Zhaojian; Zuo Gaolei; Xu Wanmei; Gong Hongju; Zhang Peng; Wang Jianghuai; Li Qingsong; Gao Chunhua; (79 pag.)CN104045552; (2019); B;,
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Electric Literature of 61837-46-5, The chemical industry reduces the impact on the environment during synthesis 61837-46-5, name is Methyl 2-bromo-4-methylpentanoate, I believe this compound will play a more active role in future production and life.

Example 37 2-(2,3-Dioxo-5-trifluoromethoxy-2,3-dihydro-indol-1-yl)-4-methyl-pentanoic acid pyrazin-2-ylamide A stirred suspension of sodium hydride (60% dispersion in oil, 208 mg) in N,N-dimethylformamide (25 mL) at 0 C. was treated with a solution of 5-trifluoromethoxy-1H-indole-2,3-dione (1.0 g) in N,N-dimethylformamide. The reaction mixture was stirred for 30 min at 0 C. and then 2-bromo-4-methyl-pentanoic acid methyl ester (prepared as in Example 9, 1.1 g) was added and it was stirred for 1 h at 0 C. It was then slowly allowed to warm to room temperature and stirred for another 3 h at room temperature. After this time, the reaction mixture was diluted with water and extracted with methylene chloride. The organic layers were combined and dried over sodium sulfate, filtered and the filterate concentrated in vacuo. The crude material was purified by column chromatography (silica gel) to afford 2-(2,3-dioxo-5-trifluoromethoxy-2,3-dihydro-indol-1-yl)-4-methyl-pentanoic acid methyl ester (1.0 g, 64%).

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, Methyl 2-bromo-4-methylpentanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kester, Robert Francis; US2012/142705; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 2216-94-6,Some common heterocyclic compound, 2216-94-6, name is Ethyl phenylpropiolate, molecular formula is C11H10O2, 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: Catalytic tests of Ni3N/NC or Ni/NC were performed as follows: 1,2-diphenylethyne (5.38mmol), Ni/NC or Ni3N/NC catalyst (7.8mol%, based on ICP results) and solvent (70mL) were mixed in a stainless-steel autoclave (100mL) equipped with an electric heating system and a magnetically driven mechanical stirrer. The reaction system was flushed with hydrogen three times and pressurized with hydrogen (2.0MPa), and then heated to 100C for hydrogenation. After the completion of reaction, it was allowed to cool to room temperature and the residual hydrogen was released. The solvent was removed under reduced pressure, and the crude products were purified by column chromatography on silica gel to withhold the catalyst. For the substrate scope, the semi-hydrogenation of alkynes was conducted using a similar method. For a typical run: the alkyne (0.3mmol), 7.8mol% Ni3N/NC-6/5-550 and ethanol (3mL) were placed in a glass vial (4mL) with cap, septum, and needle, and then two glass vials were sealed in a stainless steel autoclave (100mL) equipped with an electrical heating system, where a certain amount of ethanol was added to keep the same horizontal level of ethanol inside and outside the glass vials. Then, the reaction system was treated following the same steps as described above.

The synthetic route of 2216-94-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shi, Xiaozhen; Wen, Xin; Nie, Shilin; Dong, Jie; Li, Jingde; Shi, Yongqing; Zhang, Huiling; Bai, Guoyi; Journal of Catalysis; vol. 382; (2020); p. 22 – 30;,
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Electric Literature of 5121-34-6, These common heterocyclic compound, 5121-34-6, name is Methyl 2-amino-3-methoxybenzoate, 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.

To a solution of compound 53 (22.4 g 123 mmol) in DMF (250 mL) was added N-bromosuccinimide (21.9 g, 123 mmol) portionwise at 0 C. The mixture was stirred at 0 C for 0.5 h. To the mixture was added water and extracted with EtOAc (500 mL x 2). The combined organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the desired compound 54 (27.5 g, 86%) as a white solid.

Statistics shows that Methyl 2-amino-3-methoxybenzoate is playing an increasingly important role. we look forward to future research findings about 5121-34-6.

Reference:
Patent; GREEN CROSS CORP.GREEN CROSS CORPORATION; CHOI, SOONGYU; SONG, KWANG-SEOP; LEE, SUK HO; KIM, MIN JU; SEO, HEE JEONG; PARK, EUN-JUNG; KONG, YOUNGGYU; PARK, SO OK; KANG, HYUNKU; JUNG, MYUNG EUN; LEE, KINAM; KIM, HYUN JUNG; LEE, JUN SUNG; LEE, MIN WOO; KIM, MI-SOON; HONG, DONG HO; KANG, MISUK; (278 pag.)JP5876570; (2016); B2;,
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Ester – an overview | ScienceDirect Topics

105-53-3, name is Diethyl malonate, 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. Product Details of 105-53-3

Synthesis of 2,2-dially malonic acid diethyl ester; To a mixture of diethyl malonate (10 g, 62.5 mmol) and bromoalkane (14.25 g, 187.5 mmol) was added a concentrated solution of sodium ethoxide (8.6 g of sodium in 70 m L of ethanol) slowly with continuous stirring by maintaining the temperature in between 5-10 0C. After addition of sodium ethoxide, the reaction mixture was allowed to stir at the same temperature for another 1h after which the cold-water bath was removed and the mixture was allowed to stir overnight at EPO room temperature. The excess solvent was removed, the residue was added in water and extracted in ethyl acetate. The organic phase was dried over Na2SO4 and evaporated to give a light yellow liquid. The crude material was purified by vacuum distillation to get a colorless liquid.1H NMR (400 MHz, CDCI3): 1.24 (t, 6H), 2.64 (d, 4H), 4.18 (q, 4H), 5.07-5.14 (m, 4H), 5.59-5.73(m, 2H).Mass: 240 [M]+.

The synthetic route of 105-53-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INDIAN INSTITUTE OF TECHNOLOGY BOMBAY; WO2006/117800; (2006); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H16O3

INTERMEDIATE B-33Step 1 : ethyl 4-(5-bromopyridin-2-yloxy)cycIohexanecarboxylate (B-31)To a solution of 5-bromo-2-hydroxypyridine B-30 (1.0 g, 5.75 mmol) and ethyl 4- hydroxycyclohexanecarboxylate (990 mg, 5.75 mmol) in THF (50 mL) was added PPh3 (2.4 g, 9.150 mmol) and DIAD (1.8 mL, 9.14 mmol). The reaction mixture was stirred at RT for 17 h. The solution was then concentrated and purified by ISCO to yield ethyl 4-(5- bromopyridin-2-yloxy)cyclohexanecarboxylate as a colorless oil (1.16 g, 62percent yield, 3:2 trans:cis ratio).

According to the analysis of related databases, 3618-04-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SCHERING CORPORATION; TING, Pauline, C.; LEE, Joe, F.; ASLANIAN, Robert, G.; WO2011/31628; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 84228-44-4, name is Methyl 4-amino-3-chlorobenzoate, A new synthetic method of this compound is introduced below., Safety of Methyl 4-amino-3-chlorobenzoate

Example 42A Methyl 4-{[(6-bromo-3-methyl-2-phenylquinolin-4-yl)carbonyl]amino}-3-chlorobenzoate (0510) (0511) To a solution of 1.50 g (3.82 mmol) of the compound from example 2A and 710 mg (3.82 mmol) of 172 methyl 4-amino-3-chlorobenzoate in 15 ml of 49 DMF were added, in small portions at RT, 430 mg (3.82 mmol) of 153 potassium tert-butoxide. The mixture was stirred at RT for 15 min. Subsequently, another 215 mg (1.91 mmol) of potassium tert-butoxide were added in small portions, and the mixture was stirred at RT for a further 2 h. Thereafter, the mixture was introduced into 40 ml of a 10% 83 aqueous citric acid solution while stirring, whereupon there was precipitation of solids. After diluting with water, the solids were filtered off, washed with water and dried under reduced pressure. The crude product thus obtained was purified by means of column chromatography (100 g of silica gel, eluent: cyclohexane/ethyl acetate 85:15, Biotage). 1.60 g (80% of theory, 98% purity) of the 173 title compound were obtained. (0512) 1H-NMR (400 MHz, DMSO-d6): [ppm]=10.96 (s, 1H), 8.14-8.08 (m, 3H), 8.07-8.02 (m, 2H), 7.94 (dd, 1H), 7.66-7.61 (m, 2H), 7.60-7.50 (m, 3H), 3.90 (s, 3H), 2.48 (s, 3H). (0513) LC/MS (Method 1, ESIpos): Rt=1.32 min, m/z=509/511 [M+H]+.

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; Bayer Pharma Aktiengesekkschaft; BECK, Hartmut; THALER, Tobias; KAST, Raimund; MEIBOM, Daniel; MEININGHAUS, Mark; TERJUNG, Carsten; DELBECK, Martina; LUSTIG, Klemens; MUENSTER, Uwe; OLENIK, Britta; (100 pag.)US2017/260140; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 252881-74-6, name is tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, 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 252881-74-6, Computed Properties of C13H27NO5

To a solution of 5-hexynoic acid (100 mg, 893 mumol), WSC (257 mg, 1.34 mmol),HOBt (205 mg, 1.34 mmol) and DIPEA (622 muL, 3.60 mmol) in dry DMF (2 mL) wasadded tert-butyl-12-amino-4,7,10-trioxadodecanoate (297 mg, 1.34 mmol). The reactionmixture was stirred for 19 h at room temperature. After evaporation under reducedpressure, the reaction mixture was diluted in AcOEt and washed with sat NaHCO3 aq.,water and brine, and dried over Na2SO4. After filtration and evaporation gave compound3-5 (313 mg, 0.84 mmol, 68%) as a colorless oil.

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:
Article; Takaoka, Yousuke; Uchinomiya, Shohei; Kobayashi, Daichi; Endo, Masataka; Hayashi, Takahiro; Fukuyama, Yoshiaki; Hayasaka, Haruko; Miyasaka, Masayuki; Ueda, Takumi; Shimada, Ichio; Hamachi, Itaru; Chem; vol. 4; 6; (2018); p. 1451 – 1464;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 82702-31-6, name is Methyl 3-bromo-4-fluorobenzoate, A new synthetic method of this compound is introduced below., Safety of Methyl 3-bromo-4-fluorobenzoate

Cesium carbonate ((3.1 g, 9.6 mmol) was added to 2,4-difluorophenol (0.83 g, 6.4 mmol) and methyl 3-bromo-4-fluorobenzoate (1.57 g, 6.7 mmol)In a solution of dimethyl sulfoxide (10 mL). The reaction mixture was stirred at 80 C for 12 hr, then cooled to room temperature, then water (50mL), ethyl acetate (50mL*2). The organic phase was washed with brine (25 mL*4) and evaporated to dryness. The crude product was subjected to column chromatography (peel ether: ethyl acetate = 20:1) to give methyl 3-bromo-4-(2,4-difluorophenoxy)benzoate (1.58 g, 4. 72%).

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; Shanghai Hansen Bio-pharmaceutical Technology Co., Ltd.; Jiangsu Haosen Pharmaceutical Group Co., Ltd.; Sun Changan; Zhang Xiaoyu; Chen Gangsheng; Zong Shumin; (45 pag.)CN109836385; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics