N,N-Diethylethanamine trihydrofluoride → Ethyl-4,4-difluorocyclohexane carboxylate

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Reaction Steps

Procedure for the fluorination of carbonyls (examples 85-96): To a suspension of disubstituted aminodifluorosulfinium salt (2.0 mmol) and triethylamine trihydrofluoride (163 μL, 1.0 mmol) in dichloromethane (2.0 mL), at room temperature and under nitrogen, is added 4-carboethoxy-cyclohexanone (159 μL, 1.0 mmol). The reaction mixture was stirred 20 h, then quenched with a 5% aqueous sodium bicarbonate solution, stirred for 15 min, and the resulting mixture was extracted using dichloromethane. The organic phases were combined, dried over magnesium sulfate and filtered through a pad of silica gel. Solvents were evaporated to provide 4-carbethoxy-1,1-difluorocyclohexane admixed with 4-carboethoxy-1-fluorocyclohex-1-ene as a clear oil (refer to the following table for yields and product distribution).

Provenance & Evidence