Tetrafluoroborate → Ethyl-4,4-difluorocyclohexane carboxylate

Procedure for the fluorination of carbonyls in various solvents (examples 68-69): To a mixture of the diethylaminodifluorosulfinium tetrafluoroborate (458 mg, 2.0 mmol) and triethylamine trihydrofluoride (163 μL, 1.0 mmol) in the solvent (2.0 mL), at room temperature and under nitrogen, is added 4-carboethoxycyclohexanone (159 μl, 1.0 mmol). The reaction mixture is stirred for 23 h, then quenched with a 5% aqueous sodium bicarbonate solution, stirred for 15 min, and the resulting mixture was extracted using pentane. 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-carbethoxy-1-fluorocyclohex-1-ene as a clear oil (refer to the following table for yields and product distribution).

1. customquenched with a 5% aqueous sodium bicarbonate solution
2. stirringstirred for 15 min
3. extractionthe resulting mixture was extracted
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered through a pad of silica gel
6. customSolvents were evaporated

ORD record

ord-1054237749ef4cd6aa72d8934bf7b276

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08680332B2