4-tert-Butylcyclohexanone → 4-tert-butyl-1,1-difluorocyclohexane

Participants

Reaction Steps

To a mixture of diethylaminosulfinium tetrafluoroborate (344 mg, 1.5 mmol), triethylamine trihydrofluoride (326 μl, 2.0 mmol) and triethylamine (139 μl, 1.0 mmol) in dichloromethane (3.0 mL) at room temperature is added 4-tert-butylcyclohexanone (154 mg, 1.0 mmol). The reaction mixture is stirred for 22 hours, then an aqueous solution of sodium bicarbonate (5%) is added and stirring is continued for 15 minutes. The phases are separated and the aqueous layer is extracted twice using dichloromethane. The organic phases are combined and dried with magnesium sulphate. The solution is passed through a pad of silica gel with dichloromethane elution. Solvent are evaporated in vacuo to provide 4-t-butyl-1,1-difluorocyclohexane (160 mg, 91%) as a clear liquid, admixed with 0.8% of the corresponding vinyl fluoride.

Provenance & Evidence