Methyl iodide → 4-Bromo-2-fluoro-benzoic acid methyl ester

Participants

Reaction Steps

An ambient suspension of 4-bromo-2-fluorobenzoic acid (15.0 g, 68.5 mmol), iodomethane (21.0 mL, 342.5 mmol), and potassium carbonate (19.0 g, 137 mmol) in N,N-dimethylformamide (200 mL) was stirred at room temperature for 16 h, after which it was diluted with ethyl acetate (200 mL) and water (100 mL). The layers were separated, and the organics were washed with water (3×100 mL) and brine (1×100 mL), dried over sodium sulfate, and concentrated under reduced pressure. The residue was passed through a plug of SiO2 gel, eluting with 50% ethyl acetate in hexane, to give the title compound as a solid. MS (ESI) m/z 233 [M+H]+.

Provenance & Evidence