Methanol → Methyl 2-(4-bromophenyl)acetate

Participants

Reaction Steps

To a solution of 4-bromophenylacetic acid (50 g) in methanol (250 mL) thionyl chloride (34.2 mL) is added dropwise while the temperature of the reaction mixture is kept at 0-5° C. Upon complete addition, the cooling is removed and the mixture is allowed to warm to rt. Stirring is continued for 75 min before the solvent is removed in vacuo. The yellow oil is dissolved in benzene and evaporated. The residue is dissolved in EA, washed with water, brine, 2 N aq. Na2CO3, and brine. The organic phase is dried over MgSO4 and evaporated and dried under high vacuum at 85° C. for 30 min to give 4-bromophenylacetic acid methyl ester (52.4 g) as a yellow oil. 1H-NMR(D6-DMSO): 3.60 (s, 3H), 3.67 (s, 2H), 7.22 (d, 8.5, 2H), 7.50 (d, 8.5, 2H).

Provenance & Evidence