Water → 4-Methylpyridine-2-sulfonyl fluoride

Participants

Reaction Steps

To a solution of 2-(benzylsulfanyl)-4-methylpyridine (1.40 g) in acetic acid (10 mL)-water (5 mL) was added N-chlorosuccinimide (3.48 g) under ice-cooling, and the mixture was gradually warmed to room temperature and stirred for 4 hr. Potassium fluoride (379 mg) was added at room temperature and the mixture was stirred for 18 hr. The reaction mixture was concentrated under reduced pressure, diluted with ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate solution. The separated aqueous layer was extracted with ethyl acetate. Combined organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=4:1→11:1) to give the title compound as a crude pale-yellow oil (yield 343 mg, 30%).

Provenance & Evidence