N-bromobutanimide → Ethyl 2-(3-(bromomethyl)phenyl)acetate

Participants

Reaction Steps

A mixture of N-bromo-succinimide (10.68 g, 60.0 mmol), m-tolyl-acetic acid ethyl ester (10.0 g, 56.1 mmol; available from Aldrich Chemical Company, Inc., Milwaukee, Wis.) and benzoyl peroxide (40 mg, 0.17 mmol) in carbon tetrachloride (250 mL) was heated at reflux under nitrogen for 36 h. The reaction mixture was filtered, evaporated, and purified by chromatography on silica gel, eluting with 0-100% dichloromethane in hexane to give (3-bromomethyl-phenyl)-acetic acid ethyl ester (4.79 g, 33%). MS m/z 257. 1HNMR (DMSO-d6): δ 7.2-7.35 (m, 4H), 4.50 (s, 2H), 4.18 (q, 2H), 3.62 (s, 2H), 1.28 (t, 3H).

Provenance & Evidence