2,2,2-Trifluoroethanesulfonyl chloride → N-(4-(2,4-Difluorophenoxy)phenyl)-N-(2,2,2-trifluoroethanesulfonyl)amine

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Reaction Steps

2,2,2-Trifluoroethanesulfonyl chloride (10.0 g, 54.8 mmol) was added dropwise to a solution of 4-(2,4-difluorophenoxy)aniline (11.0 g, 50.0 mmol) and 4-dimethylaminopyridine (9.1 g, 74.6 mmol) in methylene chloride (100 mL) at 0° C. under nitrogen. The mixture was slowly warmed to room temperature, stirring for a total of 72 h. The mixture was washed with saturated aqueous sodium bicarbonate solution (200 mL), dried over MgSO4, filtered and the solvent was removed under reduced pressure to afford the crude product as an orange oil. This residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate/chloroform (1:4), to provide the title compound as a yellow solid: mp 105-108° C.; TLC Rf (1:9 ethyl acetate/chloroform)=0.75; 1H NMR (300 MHz, CDCl3) 7.23 (d, J=8.9 Hz, 2H), 7.14-6.87 (m, 3H), 6.93 (d, J=8.9 Hz, 2H), 3.76 (q, J=8.8 Hz, 2H) ppm; APCI MS m/z 366 [C14H10F5NO3S—H]−.

Provenance & Evidence