Methanol → Methyl 5-chloro-2-fluorobenzoate

Participants

Reaction Steps

To a suspension of 5-chloro-2-fluoro-benzoic acid (2.0 g, 11.5 mmol) in dichloromethane (50 ml) was added a solution of oxalyl chloride in dichloromethane (2 M, 6.5 ml, 13 mmol) followed by N,N-dimethylformamide (5 drops). After stirring for 1 hour, methanol (10 ml) was added. After stirring for 20 hours, the mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate (200 ml) and saturated aqueous potassium carbonate solution (100 ml). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to provide methyl 5-chloro-2-fluoro-benzoate (2.0 g, 92% yield).

Provenance & Evidence