Synthesis of methyl 2-bromobutyrate

Preparation of methyl 2-bromobutyrate

Preparation of methyl 2-bromobutyrate

Preparation of methyl 2-bromobutyrate

70.4 g of butyric acid are added to 112 g thionyl chloride during 75 min, with stirring, at room temperature, then the mixture is heated on a boiling water-bath for 30 min, after which the thionyl chloride excess is distilled off. 135 g of bromine are added to the residue at 80-90° C, with stirring, and the whole is heated for 5 hours on a boiling water-bath, then cooled. 46 ml of methanol are added, and the solution is heated under reflux for 2 hours. A small upper layer is formed and is separated in a separatory funnel and discarded. The remainder is distilled in a vacuum after a small forerun has been removed at 100° C under atmospheric, pressure yielding methyl 2-bromobutyrate (75-86%) with b.p. 70-75°/15 mm.

Arch. Pharm., 292, 569, 570 (1959).

IUPAC Name

methyl 2-bromobutanoate

InChI

InChI=1S/C5H9BrO2/c1-3-4(6)5(7)8-2/h4H,3H2,1-2H3

InChI Key

UFQQDNMQADCHGH-UHFFFAOYSA-N

Canonical SMILES

CCC(C(=O)OC)Br

Depositor-Supplied Synonyms

Methyl 2-bromobutyrate, Methyl 2-bromobutanoate, 3196-15-4, 2-Bromobutyric Acid Methyl Ester, Methyl-2-bromobutyrate, Butanoic acid, 2-bromo-, methyl ester, UFQQDNMQADCHGH-UHFFFAOYSA-N, alpha-bromobutyric acid methyl ester, SBB070737, Methyl bromobutyrate, methyl-2-bromobutanoate, PubChem20191, AC1L3UMU, AC1Q2RUF, methyl alpha-bromobutyrate, methyl 2-bromo-n-butyrate, Methyl 2-bromobutanoate #, 2-bromobutyrate-methyl ester, 2-Bromobutyricacidmethylester, ACMC-1B79G, METHYL2-BROMOBUTYRATE, KSC490A4D, SCHEMBL532563, 237310_ALDRICH, AC1Q244X, Jsp005934, CTK3J0041, 2-bromo-butyric acid methyl ester, MolPort-001-770-245, NSC21974, EINECS 221-699-0, ANW-27236, AR-1J4709, MFCD00009666, NSC 21974, NSC-21974, AKOS001270829, AKOS016842317, CS14136, RP24205, RTR-013494, TRA0046210, METHYL (+/-)-2-BROMOBUTYRATE, AK-41627, BC004510, BR-41627, OR025194, OR128777, OR328385, 2-BROMO-N-BUTYRIC ACID METHYL ESTER, KB-202740, ST2413290, TR-013494, AM20090460, B1462, FT-0611545, FT-0628433, W5381, S-1351, I04-0302, I14-6073, Q-201370, 3B3-020349, InChI=1/C5H9BrO2/c1-3-4(6)5(7)8-2/h4H,3H2,1-2H

Removed Synonyms

2-Bromo methyl butyrate, C5H9BrO2, Butanoic acid, methyl ester, CID95577, 69043-96-5, 21249-59-2, 71334-38-8

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