Methyl iodide → 1-Bromo-4-chloro-2-fluoro-3-methoxybenzene

Participants

Reaction Steps

A heterogeneous mixture of 3-bromo-6-chloro-2-fluorophenol (14.4 g, 0.064 mol), methyl iodide (13.5 g, 0.096 mol) and potassium carbonate (8.8 g, 0.064 mol) in acetonitrile (100 mL) was heated under reflux for two hours. The mixture was cooled, diluted with water (100 mL) and extracted with diethyl ether (2×150 mL). The combined extracts were dried and concentrated. The dark oil was purified by chromatography (5% ethyl acetate in hexanes) to give 1-bromo-4-chloro-2-fluoro-3-methoxybenzene (14.8 g, 0.062 mol) 1H NMR (CDCl3): δ 7.20 (m, 1H), 7.10 (dd, 1 H), 4.0 (s, 3H).

Provenance & Evidence