Methanol → Methyl 2-chloro-3-nitrobenzoate

Participants

Reaction Steps

A slurry of 20 g (99 mmol) of 2-chloro-3-nitrobenzoic acid in 800 mL dichloromethane was cooled in an ice bath. Dimethylformamide (0.40 mL) was added to the reaction followed by drop wise addition of 13.85 g (109 mmol) of oxalyl chloride. The reaction was allowed to warm to room temperature and was stirred for 6 h. Methanol (200 mL) was added drop wise and the reaction was stirred overnight. The reaction was concentrated to a residue, dissolved in dichloromethane and passed through a plug of silica eluting with a 50% ethyl acetate/hexane mixture. The filtrate was concentrated in vacuo to give 21.5 g (100%) of the title compound.

Provenance & Evidence