Dimethylformamide → Methyl 4-chloro-3-(methylsulfonyl)benzoate

Participants

Reaction Steps

A round bottom flask was charged with 4-chloro-3-sulfinobenzoic acid (12 g, 54.0 mmol), potassium carbonate (15.4 g, 109 mmol) and N,N-dimethylformamide (170 mL). Methyl iodide (16.1 mL, 218 mmol) was added slowly and the reaction was stirred for 4 hours. The reaction mixture was then diluted with water and extracted with EtOAc. The combined organic layers were concentrated under reduced pressure to get the intermediate methyl-4-chloro-3-(methylsulfonyl)benzoate as an off white solid. This was dissolved in methanol (100 mL) and 6N sodium hydroxide (50 mL) was added and the reaction was stirred for 3 hours. Methanol was removed under reduced pressure and water was added to the residue. The resulting mixture was then acidified with 2N HCl at 0° C. and the solid formed was filtered and dried to get the title compound as a white solid.

Provenance & Evidence