Benzoyl chloride → N-(4-fluoro-3-nitrophenyl)benzamide

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To a solution of 4-fluoro-3-nitroaniline (2.00 g, 12.8 mmol) and Et3N (1.98 mL, 14.1 mmol) in THF (40 mL) was added benzoyl chloride (1.58 ml, 13.5 mmol) dropwise at 5° C. The mixture was stirred at 5° C. for 1 hour, warmed to room temperature, and then evaporated. The residue was suspended in H2O (100 ml), adjusted to pH 2, and then extracted with EtOAc. The extract was washed with H2O, 10% NaHCO3 and brine, dried over MgSO4, and concentrated under vacuum to give the crude product, which was purified by washing with i-Pr2O to give the title compound as pale brown crystal (2.70 g, 81%).

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