N-bromobutanimide → Methyl 2-(bromomethyl)-4-methoxybenzoate

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-methoxy-2-methyl-benzoic acid methyl ester (20 g, 111 mmol), N-bromosuccinimide (20.7 g, 117 mmol) and dibenzoylperoxide (0.54 g, 2 mmol) in CCl4 (150 mL) was irradiated with a 300 W lamp. The reaction maintains a steady reflux and after 4.5 h, the lamp was removed and the mixture cooled to 5° C. The mixture was then filtered, the filtrate evaporated and the residue purified twice by chromatography (SiO2, Heptane:Diethyl ether: 95:5 to 85:15) to afford the title product (16.6 g, 58%) as a white solid. MS m/e=258.1 (M−H+).

Provenance & Evidence