Sulfuric Acid → 6-Acetyl-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid methyl ester

Participants

Reaction Steps

A mixture of 2-(2-chlorophenylamino)-3,4-difluoro-6-trimethylsilanylethynylbenzoic acid methyl ester (1.00 g, 2.54 mmol), HgSO4 (761 mg, 2.54 mmol), and concentrated H2SO4 (0.27 mL) in acetone-water (22 mL/4 mL) was refluxed for 3 hours. The reaction mixture was concentrated in vacuo, diluted with EtOAc-THF, and washed with water and brine. The organic layer was dried over MgSO4, filtered, and concentrated to give the crude material that was purified by silica gel flash column chromatography (8% EtOAc in hexanes) to afford the desired product (496 mg, 58%).

Provenance & Evidence