Water → 2-[2-(4-Fluorophenylthio)-6-fluorophenyl]-4,4-dimethyloxazoline

Participants

Reaction Steps

To a solution of 4-fluorothiophenol (3.64 g, 28.4 mmol) in 50 ml of dry THF at -78° C. is added n-butyllithium (17.8 ml of a 1.6M solution in hexane). After 30 minutes, 2-(2,6-difluorophenyl)-4,4-dimethyloxazoline (5.0 g, 23.7 mmol) in 10 ml of dry THF is added dropwise. The reaction mixture is allowed to warm to room temperature and then is heated to 60° C. for 5.5 hours. After cooling, the reaction mixture is poured into water and then extracted with diethyl ether. The extracts are washed with water and then brine, and dried over MgSO4 to afford the crude product. Chromatography over silica gel eluting with 10:1 hexane/ethyl acetate afforded the subtitle compound.

Provenance & Evidence