3196-15-4 Archives - Page 2 of 3 - Esters-buliding-blocks

A new synthetic route of 3196-15-4

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. 3196-15-4, name is Methyl 2-bromobutyrate, A new synthetic method of this compound is introduced below., Formula: C5H9BrO2

Weighed 2,4-dichlorophenol (815mg, 5mmol) in 100mL round bottom flask was added anhydrous potassium carbonate (1.38g, 10.0mmol, 2eq), acetone (30 mL) and 2-bromo-butyric acid methyl ester ( 995.6mg, 5.5mmol, 1.1eq), was heated under reflux for 12 hours.The reaction was cooled to room temperature, the solid was removed by suction filtration, and the filtrate was evaporated to dryness after the addition of water (30 mL), extracted with ethyl acetate (50mL × 3), combined extracts were washed with water (20mL × 2) and saturated brine (20 mL ) was washed, dried over anhydrous sodium sulfate, filtered and concentrated, the crude product was purified by silica gel column chromatography [V (ethyl acetate) :V (petroleum ether) = 1: 8] to give 1.22g, 93% yield.1HNMR (400MHz, CDCl3)

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; Changzhou University; Chen, Xi; Liang, Cuirong; Yang, Qinghong; Ren, Jie; Jin, Guihua; Huang, Qianhui; Xu, Yuanyuan; Hu, Kun; (32 pag.)CN105440020; (2016); A;,
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The important role of 3196-15-4

Application of 3196-15-4,Some common heterocyclic compound, 3196-15-4, name is Methyl 2-bromobutyrate, molecular formula is C5H9BrO2, 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.

[286] Step 3: methyl 2-[5-bromo-2-(4-methylbenzoylimino)benzo[d]thiazol-3(2H)-yl]butanoate[287] To a stirred solution of N-(5-bromobenzo[d]thiazol-2-yl)-4-methylbenzamide (90 mg, 0.258 mmol) prepared in Step 2 in N,N-dimethylformamide (3.0 mL) were added methyl 2-bromobutyrate (93.9 mg, 0.519 mmol) and potassium carbonate (107 mg, 0.768 mmol). The reaction mixture was stirred at 80 ? for 3 hours. The reaction mixture was quenched with water and then extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered, and then evaporated. The residue was purified with silica gel column chromatography (n-hexane/ethyl acetate = 10/1) to give 109.5 mg of the titled compound as a white solid (Yield: 94%)[288] 1H NMR (CDCl3, 400 MHz) delta 8.18(d, 2H), 7.56(d, 1H), 7.42(s, 2H), 7.28(d, 2H), 5.46(brs, 1H), 3.67(s, 3H), 2.47-2.54(m, 2H), 2.42(s, 3H), 0.92(t, 3H)

The synthetic route of 3196-15-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YUHAN CORPORATION; HUR, Youn; KIM, Dong-Hyun; KIM, Eun-Kyung; PARK, Jin-Hwi; JOO, Jae-Eun; KANG, Ho-Woong; OH, Se-Woong; KIM, Dong-Kyun; AHN, Kyoung-Kyu; WO2013/43001; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

The important role of 3196-15-4

Synthetic Route of 3196-15-4,Some common heterocyclic compound, 3196-15-4, name is Methyl 2-bromobutyrate, molecular formula is C5H9BrO2, 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.

Compound I-CC (3.1 g, 17.1 mmol) and aniline (1.59 g, 17.1 mmol) were dissolved in 30 mL of acetonitrile in a glass pressure tube. After the addition of potassium carbonate (4.71 g, 34.2 mmol) and potassium iodide (0.283 g, 1.71 mmol), the tube was sealed and mixture was stirred for 18 hr at 100 C. The reaction mixture was diluted with ethyl acetate and washed with saturated sodium bicarbonate solution. The organic phase was dried over a2S04, filtered, evaporated down and purified by silica column (hexane:EtOAc) to give Compound II-CC (1.97 g, 59%); LCMS:194.12 m/z (M+H)+.

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-bromobutyrate, its application will become more common.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; GALEMMO, Robert, A., Jr.; ARTIS, Dean, Richard; YE, Xiaocong, Michael; AUBELE, Danielle, L.; TRUONG, Anh, P.; BOWERS, Simeon; HOM, Roy, K.; ZHU, Yong-Liang; NEITZ, R., Jeffrey; SEALY, Jennifer; ADLER, Marc; BEROZA, Paul; ANDERSON, John, P.; WO2011/79114; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

The important role of 3196-15-4

Related Products of 3196-15-4, 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. 3196-15-4 name is Methyl 2-bromobutyrate, 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.

Step 1: a mixture of 5-bromobenzo[d]thiazol-2-amine and 7-bromobenzo[d]thiazol-2-amine [0484] To a stirred solution of 1-(3-bromophenyl)thiourea (1.00 g, 4.33 mmol) in dichloromethane (15 mL) was added dropwise a solution of bromine (345 mg, 4.33 mmol) in dichloromethane (15 mL). The reaction mixture was stirred at room temperature overnight. The resulting solid was filtered, washed with dichloromethane, and then dried under reduced pressure to give 809 mg of the titled compound as a yellow solid (Yield: 82%). Step 2: a mixture of N-(5-bromobenzo[d]thiazol-2-yl)-4-methylbenzamide and N-(7-bromobenzo[d]thiazol-2-yl)-4-methylbenzamide [0485] To a solution of the mixture of 5-bromobenzo[d]thiazol-2-amine and 7-bromobenzo[d]thiazol-2-amine (100 mg, 0.436 mmol) prepared in Step 1 in toluene (2.2 mL), were added p-toluoyl chloride (135 mg, 0.872 mmol) and diisopropylethylamine (0.22 mL, 1.38 mmol). The reaction mixture was stirred at 80 C. for 2 hours. The reaction mixture was quenched with water and then extracted with dichloromethane. The extract was dried over anhydrous sodium sulfate, filtered, and then evaporated. The residue was used in the next step without further purification. Step 3: methyl 2-[7-bromo-2-(4-methylbenzoylimino)benzo[d]thiazol-3(2H)-yl]butanoate [0486] To a solution of the mixture of N-(5-bromobenzo[d]thiazol-2-yl)-4-methylbenzamide and N-(7-bromobenzo[d]thiazol-2-yl)-4-methylbenzamide (90 mg, 0.258 mmol) prepared in Step 2 in N,N-dimethylformamide (3.0 mL), were added methyl 2-bromobutyrate (93.9 mg, 0.519 mmol) and potassium carbonate (107 mg, 0.768 mmol). The reaction mixture was stirred at 80 C. for 3 hours. The reaction mixture was quenched with water and then extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, filtered, and then evaporated. The residue was purified with silica gel column chromatography (n-hexaneethyl acetate=10/1) to give 26.7 mg of the titled compound as a white solid (Yield: 23%). [0487] 1H NMR (CDCl3, 400 MHz) delta 8.19 (d, 2H), 7.45 (d, 1H), 7.20-7.34 (m, 4H), 5.53 (brs, 1H), 3.67 (s, 3H), 2.47-2.54 (m, 2H), 2.43 (s, 3H), 0.91 (t, 3H)

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

Reference:
Patent; YUHAN CORPORATION; Hur, Youn; Kim, Dong-Hyun; Kim, Eun-Kyung; Park, Jin-Hwi; Joo, Jae-Eun; Kang, Ho-Woong; Oh, Se-Woong; Kim, Dong-Kyun; Ahn, Kyoung-Kyu; US2015/11528; (2015); A1;,
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A new synthetic route of 3196-15-4

Double-benzyl-isoquinoline (Formula in, X = Br) 6.85g, 2- bromo-7-bromo-butyrate weighed 4.50g wasdissolved in N, N- dimethyl Formamide 100mL, 500mL three-neck flask was added, mixed by stirring, cooled to-10 C, and the reaction was stirred 24h incubation After filtration, filtrate was washed with a small amount of5% hydrobromic acid and, the solvent was distilled off under reduced pressure to a volume of the liquid reducedto 1/4, crystallization at room temperature 8h, Filtered and the filtrate evaporated under reduced pressure to 50%of water, cooled to 5 C to crystallize overnight, filtered and the solid was dried at 60 C 4h, to give the lightThe product 5.20g yellow powder in a yield of 70.29%, a purity of 96.47% (HPLC).

Reference:
Patent; Shandong Normal University; LIU, YUFA; ZHANG, MENG; MAO, FEIFEI; CHEN, DONGMEI; ZHANG, JINE; (22 pag.)CN103910740; (2016); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

The important role of 3196-15-4

Reference of 3196-15-4, The chemical industry reduces the impact on the environment during synthesis 3196-15-4, name is Methyl 2-bromobutyrate, I believe this compound will play a more active role in future production and life.

5-Ethyl-2-pyrazin-2-yl-thiazol-4-ol: A solution of pyrazine-2-carbothioamide (1 g, 7.19 mmol) in ethanol (20 ml) was treated with methyl 2-bromobutyrate (1.56 g, 992 mul, 8.62 mmol) an pyridine (853 mg, 872 mul, 10.8 mmol) and heated to reflux for 2 hours. The reaction mixture was cooled and concentrated to dryness under reduced pressure, and the resulting solid was filtered and washed with diethyl ether to provide 5-ethyl-2-pyrazin-2-yl-thiazol-4-ol (0.740 g, 50%) which was used directly without further purification. MS (M+H)=208.

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-bromobutyrate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hoffmann-La Roche Inc; Bhagirath, Niala; Brameld, Kenneth Albert; Kennedy-Smith, Joshua; US2013/90334; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Extracurricular laboratory: Synthetic route of Methyl 2-bromobutyrate

The synthetic route of 3196-15-4 has been constantly updated, and we look forward to future research findings.

3196-15-4, name is Methyl 2-bromobutyrate, 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 3196-15-4

General procedure: As part of this general procedure, the appropriate diphenyl diselenide (9.5 mmol) dissolved in a 1:1 mixture of water and THF (50 mL) underprotective nitrogen gas, sodiumborohydride (47.5 mmol) was added and the mixture was stirred for around 35 minutes while observing adecolorization in the first 1-3 minutes. Next, a solution of a methyl -2-bromo-acetate derivatives (19.37 mmol) in THF or DCM (5 mL) wasadded and the reaction was stirred at room temperature and monitored via thin layer chromatography (TLC). Upon consumption of the startingmaterial usually occuring after 24-48 hours, the reaction mixture was diluted with 50 mL of a saturated aqueous solution of ammoniumchloride and extracted with diethyl ether. The combined organic extracts dried over sodium sulfate, and the solvent was evaporated under reducedpressure to obtain the desired intermediate, which was used without further purification.

The synthetic route of 3196-15-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ali, Wesam; Battistelli, Cecilia; D?browska, Monika; Handzlik, Jadwiga; Honkisz-Orzechowska, Ewelina; Jacob, Claus; Kincses, Annamaria; Latacz, Gniewomir; Nove, Marta; Rasile, Manuela Monica; Romanelli, Annalisa; Spengler, Gabriella; Starek, Ma?gorzata; Szyma?ska, Ewa; Zwergel, Clemens; European Journal of Medicinal Chemistry; vol. 200; (2020);,
Ester – Wikipedia,
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New downstream synthetic route of 3196-15-4

Step 2: methyl 2-(2-((4-methylbenzoyl)imino-6-(methylcarbamoyl(2H)-yl)butanoate To a solution of N-methyl-2-(4-methylbenzamido)benzo[d]thiazol-6-carboxamide (185 mg, 0.57 mmol) prepared in Step 1 in N,N-dimethylformamide (2.0 mL) were added potassium carbonate (236 mg, 1.71 mmol) and methyl 2-bromobutyrate (98 uL, 0.86 mmol). The reaction mixture was stirred at 80 C. overnight and cooled to room temperature. The reaction mixture was quenched with water and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then evaporated. The residue was purified with silica gel column chromatography (n-hexaneethyl acetate=8/1?1/1, v/v) to give 160 mg of the titled compound as a white solid (Yield: 66%). 1H NMR (CDCl3, 400 MHz) delta 8.20 (s, 1H), 8.08 (d, 2H), 7.90 (d, 1H), 7.27 (d, 1H), 7.18-7.25 (m, 2H), 6.94-6.95 (m, 1H), 5.53 (m, 1H), 3.57 (s, 3H), 2.91 (d, 3H), 2.39-2.46 (m, 2H), 2.34 (s, 3H), 0.82 (t, 3H)

Brief introduction of 3196-15-4

Synthetic Route of 3196-15-4, The chemical industry reduces the impact on the environment during synthesis 3196-15-4, name is Methyl 2-bromobutyrate, I believe this compound will play a more active role in future production and life.

EXAMPLE 62a; Preparation of intermediate 2-(4-chloro-2-formyl-phenoxy)-butyric acid methyl ester; A mixture of 5-chloro-2-hydroxy-benzaldehyde (156 g, 1 mol), 2-bromo-butyric acid methyl ester (271 g, 1.5 mol), KI (2 g, 0.012 mol) and K2CO3 (276 g, 2 mol) in DMF (500 mL) was heated at 130 C. for 2 h. After cooled to room temperature, the mixture was concentrated. The residue was partitioned between EtOAc and water. The organic layer was washed with water, brine, dried over anhydrous Na2SO4 and concentrated to give the title compound (240 g).

Reference:
Patent; Chen, Li; Han, Xingchun; He, Yun; Yang, Song; Zhang, Zhuming; US2009/163512; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Analyzing the synthesis route of Methyl 2-bromobutyrate

3196-15-4, A common compound: 3196-15-4, name is Methyl 2-bromobutyrate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

[459] Step 1: methyl 2-{5-nitro-2-[(4-methylbenzoyl)imino]benzo[d]thiazol-3(2H)-yl}butanoate[460] To a stirred solution of 4-methyl-N-(5-nitrobenzo[d]thiazol-2-yl)benzamide (0.96 g, 3.06 mmol) prepared in Preparation 10 in N,N-dimethylformamide (30 mL), were added potassium carbonate (930 mg, 6.73 mmol) and methyl 2-bromobutyrate (0.76 mL, 6.13 mmol). The reaction mixture was stirred at 50 ? for 5 hours. The reaction mixture was and quenched with water and then extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and then evaporated. The residue was purified with silica gel column chromatography (n-hexane/ethyl acetate/dichloromethane = 5/1/2) to give 830 mg of the titled compound as a yellow solid (Yield: 66%). [461] 1H NMR (CDCl3, 400 MHz) delta 8.20(m, 4H), 7.85(d, 1H), 7.30(d, 2H), 5.54(brs, 1H), 3.71(s, 3H), 2.57(m, 2H), 2.44(s, 3H), 0.94(t, 3H)