Category: 2969-81-5

Adding a certain compound to certain chemical reactions, such as: 2969-81-5, name is Ethyl 4-bromobutyrate, 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 2969-81-5, HPLC of Formula: C6H11BrO2

A mixture of 4-chlorophenol (10 g, 78 mmol) and ethyl 4-bromobutanoate (22.8 g, 117 mmol) in ethanol (100 mL) with K2CO3 (16.1 g, 1 17 mmol) was refluxed for 12 hours. The reaction mixture was cooled and filtered. The filtrate was concentrated under reduced pressure. To the residue was added ethyl acetate (100 mL) and 0 (70 mL). The two phases were separated, and the aqueous phase was extracted with ethyl acetate (3 x 40 mL). The combined organic phases were combined, dried over anhydrous Na2SO/t, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Si(, petroleum ether:ethyl acetate = 100: 1 to 5: 1) to give the title compound (10 g, 39.1 mmol, 50% yield).JH NMR (400MHz, DMSO- ) delta ppm = 7.33 – 7.27 (m, 2H), 6.96 – 6.90 (m, 2H), 4.06 (q, J=7.1 Hz, 2H), 3.97 (t, J=6.3 Hz, 2H), 2.44 (t, J=7.3 Hz, 2H), 1.95 (quin, J=6.8 Hz, 2H), 1.17 (t, J=7.1 Hz, 3H).

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Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; PLIUSHCHEV, Marina, A.; FROST, Jennifer, M.; TONG, Yunsong; BLACK, Lawrence, A.; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; CHUNG, Seungwon; XIONG, Zhaoming; SWEIS, Ramzi, Farah; DART, Michael, J.; BROWN, Brian, S.; MURAUSKI, Kathleen; (673 pag.)WO2019/90069; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 2969-81-5, 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. 2969-81-5, name is Ethyl 4-bromobutyrate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 4-chlorophenol (10 g, 77.784 mmol, 1 equiv) in N,N- dimethylformamide (100 mL) was added anhydrous potassium carbonate (21 .5 g, 1 16.6 mmol, 2 equiv) and ethyl 4-bromobutanoate (16.7 mL, 1 16.677 mmol, 1 .5 equiv). The reaction mixture was heated to 140 C and stirred for 4 h. The progress of the reaction was monitored by TLC. After completion of reaction, the reaction mixture was allowed to cool to 27 C, filtered the solid and washed with ethyl acetate (700 mL). The filtrate was washed with water (2 x 200 mL), brine solution (100 mL), dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography using 10 % ethyl acetate in hexane as eluent to obtain ethyl 4-(4-chlorophenoxy)butanoate (17.0 g, 89 % yield) as white solid. LCMS (ES) m/z = 243.1 [M+H]+. NMR (400 MHz, CDCI3): delta ppm 1 .25 (t, J = 7.2 Hz, 3 H), 2.06 – 2.12 (m, 2 H), 2.49 (t, J = 7.6 Hz, 2 H), 3.97 (t, J = 6.0 Hz, 2 H), 4.1 1 – 4.17 (m, 2 H), 6.80 (d, J = 8.8 Hz, 2 H), 7.21 (d, J = 8.8 Hz, 2 H).

The chemical industry reduces the impact on the environment during synthesis Ethyl 4-bromobutyrate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; AXTEN, Jeffrey; CHEUNG, Mui; DEAN, Anthony W.; DEMARTINO, Michael P.; EIDAM, Hilary Schenck; KETHIRI, Raghava Reddy; KALITA, Biswajil; KRISTAM, Rajendra; (162 pag.)WO2017/212423; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics