(Diethylamino)sulfur trifluoride → 4-(fluoromethyl)-5-[3-(trifluoromethoxy)phenoxy]-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole

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Reaction Conditions

Reaction Steps

To a stirred solution of 5-[3-(trifluoromethoxy)phenoxy]-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole-4-methanol (i.e. the product of Example 5, Step I, 0.075 g, 0.18 mmol) in anhydrous dichloromethane (4 mL) cooled to −78° C. was added (diethylamino)sulfur trifluoride (0.032 mL, 0.24 mmol). The mixture was stirred for 2 h during which time the temperature increase to −30° C. The reaction mixture was diluted with saturated aqueous sodium bicarbonate solution (5 mL), extracted with ethyl acetate (3×15 mL), and washed with saturated aqueous sodium chloride solution (10 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure to afford the crude product which was purified by chromatography on silica gel eluting with 0 to 10% ethyl acetate in hexanes to obtain the title compound (0.052 g) as a yellow solid.

Provenance & Evidence