Triethylamine → 2-Fluoro-1-(2-fluoro-phenyl)-ethanone

A solution of 1-(2-fluorophenyl)-2-hydroxyethanone [CAS 218771-68-7; WO9857925, ex. 16) (2.77 g, 18.0 mmol) in dichloromethane (42 ml) was treated consecutively at 0° C. with triethylamine (6.36 g, 62.8 mmol), triethylamine trihydrofluoride (3.05 g, 18.0 mmol) and nonafluoro-n-butansulfonylfluoride (8.48 g, 26.9 mmol). The tube was sealed and the reaction mixture stirred overnight at room temperature. For the workup, the dark red solution was poured on a saturated solution of sodium hydrogencarbonate and ice, then extracted with dichloromethane. The organic layer was separated, dried over sodium sulphate and evaporated. The crude material was purified by flash chromatography on silica gel (Telos Flash Silica) using dichloromethane as the eluent to give the 2-fluoro-1-(2-fluoro-phenyl)-ethanone (1.23 g, 61% of theory) as a yellow semisolid.

1. customThe tube was sealed
2. extractionextracted with dichloromethane
3. customThe organic layer was separated
4. dry with materialdried over sodium sulphate
5. customevaporated
6. customThe crude material was purified by flash chromatography on silica gel (Telos Flash Silica)

ORD record

ord-519f76ae48314aca99c27b8ae1c7e844

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08754075B2