Hydrochloric Acid → 2-Phenyl-ethenesulfonic acid 4-chloro-2-fluoro-benzoylamide

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To a solution of 2-phenyl-ethenesulfonic acid amide (500 mg, 2.7 mmol) in dioxane (25 ml) sodium hydride (197 mg, 55% dispersion in mineral oil) were added and the mixture was stirred at room temperature for 30 minutes. 4-Chloro-2-fluoro-benzoyl chloride (527 mg, 2.7 mmol) were added and the mixture was stirred at room temperature overnight. After addition of water (50 ml) the pH was adjusted to 7 with 1 N HCl and the mixture was extracted with ethyl acetate (3 times 50 ml). The combined organic phases were dried over Na2SO4 and concentrated in vacuo. Preparative HPLC (RP18, methanol-water-gradient) returned the title compound (730 mg, 79% yield) as a white solid.

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