Dimethylformamide → Methyl 3-fluoro-4-methoxybenzoate

Participants

Reaction Steps

A mixture of 3-fluoro-4-hydroxybenzoic acid (500 mg, 3.2 mmol), cesium carbonate (3.1 g, 9.6 mmol) and iodomethane (440 μl, 7.0 mmol) in dimethylformamide (7 mL) was stirred at room temperature for 4 hours. The mixture was diluted with ethyl acetate and washed with 5% aqueous lithium chloride, 1N aqueous sodium hydroxide, brine, then dried over anhydrous sodium sulfate. Filtration and concentration afforded 534 mg, 2.9 mmol (92%) of methyl 3-fluoro-4-(methyloxy)benzoate. MS (EI) for C9H9FO3: 185 (MH+).

Provenance & Evidence