Trifluoroacetic anhydride → 5-Bromo-2-methylpyridin-1-ium-1-olate

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-2-methylpyridine (1 g, 5.81 mmol) and urea hydrogen peroxide (1.1 g, 12.2 mmol) in DCM (30 mL) at 0° C. was added trifluoroacetic anhydride (1.6 mL, 11.6 mmol). After warming to 25° C. over 12 h, the solution was partitioned between H2O-DCM. The aqueous phase was washed several times with DCM and the combined organic fractions were dried over Na2SO4, concentrated and purified via column chromatography (silica, 1% MeOH in DCM (1% NH4OH)) yielding the title compound (660 mg, 60%) as a white solid: LCMS (ES) m/z=190 (M+H)+.

Provenance & Evidence