Benzoyl Peroxide → Methyl bromo(4-bromophenyl)acetate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-(4-bromophenyl)acetate (9 g, 39.5 mmol) in carbon tetrachloride was added N-bromosuccinimide (7.1 g, 40 mmol), benzoyl peroxide (1.2 g, 6.7 mmol). The mixture was heated to reflux, and then stirred at the 77° C. for 4 hours. Thin layer chromatography showed full conversion. Then the mixture was concentrated under vacuum. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=20/1) to give methyl 2-bromo-2-(4-bromophenyl)acetate (12 g, 91%). 1H NMR (300 MHz, CDCl3) δ 7.68-7.65 (m, 2H), 7.52-7.49 (m, 2H), 5.35-5.31 (m, 1H), 3.89 (s, 3H).

Provenance & Evidence