Pyridine → N-(3-bromo-2-fluoro-phenyl)-2,5-difluoro-benzenesulfonamide

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Reaction Steps

3-Bromo-2-fluoroaniline (10 g, 52.63 mmol) was dissolved in DCM (100 mL) under nitrogen atmosphere. Dry pyridine was added (6 mL, 73.68 mmol, 1.4 eq), followed by 2,5-difluorobenzenesulfonyl chloride (7.08 mL, 52.63 mmol, 1 eq) and the mixture was stirred at r.t. for 2 h. It was then diluted with DCM and washed with aqueous 0.5 N HCl (3×80 mL) and brine. The organic layer was dried over Na2SO4 and evaporated to dryness. The solid was taken up with ethyl ether and stirred for 30 minutes. It was then filtered and dried at 40° C. under reduced pressure to give 17.8 g of N-(3-bromo-2-fluoro-phenyl)-2,5-difluoro-benzenesulfonamide as a pale yellow solid (92%). HPLC (254 nm): Rt: 6.28 min; 1H NMR (DMSO-d6) Shift: 10.86 (s, 1H), 7.50-7.73 (m, 4H), 7.23-7.31 (m, 1H), 7.12 (dt, J=1.3, 8.1 Hz, 1H).

Provenance & Evidence