Methyl iodide → Methyl 4-fluoro-3-nitrobenzoate

Participants

Reaction Steps

Potassium carbonate (149 g, 1.08 mol) and iodomethane (252 mL, 4.05 mol) were added to a solution of 4-fluoro-3-nitrobenzoic acid (50 g, 0.27 mol) in dry acetone (700 mL) under argon. Overhead mechanical stirring was carried out for 16 hours. The reaction mixture was filtered, and acetone was removed under vacuum. The residue was partitioned between ethyl acetate and saturated potassium carbonate solution, the aqueous layer was washed with ethyl acetate, the combined organic layers were washed with saturated potassium carbonate solution, brine, dried over sodium sulfate, and concentrated to yield the title compound as a light yellow solid; m.p. 58.5°-59.50° C.

Provenance & Evidence