Methanol → 2-Fluoro-3-(propane-1-sulfonylamino)-benzoic acid methyl ester

Participants

Reaction Steps

To a 2-fluoro-3-(propane-1-sulfonylamino)-benzoic acid (19, 5.05 g, 19.3 mmol) in 100 mL of dichloromethane, N,N-dimethylformamide (0.075 mL, 0.97 mmol) was added under an atmosphere of nitrogen. The reaction was cooled with ice/water, followed by slow addition of oxalyl chloride (2.00 M in dichloromethane, 10.8 mL, 21.6 mmol). The reaction mixture was stirred at room temperature for 3.0 hours. The reaction was cooled with ice/water, followed by addition of methanol (36.0 mL, 0.89 mol) slowly. The reaction was stirred at room temperature overnight. The reaction was concentrated under vacuum and purified with silica gel column chromatography eluting with 30% ethyl acetate in hexane to give the desired compound as a crude white solid (20, 4.0 g), used in the next step without further purification.

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