Triethylamine → 1-Cyclooctene

Procedure for the fluorination of alcohols in various solvents (examples 62-67): To a mixture of the diethylaminodifluorosulfinium tetrafluoroborate (344 mg, 1.5 mmol), triethylamine trihydrofluoride (326 μL, 2.0 mmol) and triethylamine (139 μL, 1.0 mmol) in the solvent (3.0 mL), at room temperature and under nitrogen, is added cyclooctanol (132 μl, 1.0 mmol). The reaction mixture is stirred for 24 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 fluorocyclooctane of admixed with cyclooctene 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-3f6d3d5690004a85a4b121a4251826ae

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08680332B2