Potassium Bromide → 2,2,2-Trifluoro-1-(2-fluoro-5-(4-fluorobenzoyl)phenyl)ethanone

Participants

Reaction Steps

A homogeneous yellow solution of crude 2,2,2-trifluoro-1-(2-fluoro-5-((4-fluorophenyl)(hydroxy)methyl)phenyl)ethanone (1.15 g, 3.64 mmol, Intermediate 35: step b) and TEMPO (18.4 mg, 0.118 mmol) in DCM (7.3 mL) was stirred on an ice bath while a solution of aqueous KBr (43 mg, 0.36 mmol) in 1 M aqueous NaHCO3 (1.27 mL, 1.27 mmol) was added in one portion. NaOCl [4.6 mL, 0.89 M (6.15% w/w Clorox bleach), 4.1 mmol] was then added dropwise over 5 minutes to the homogeneous bilayer. After 20 minutes stirring on the ice bath, the clear yellow organic layer was collected, and the aqueous layer extracted with DCM (1×6 mL). The combined organic layers were washed with 5 M aqueous NaCl (1×3 mL), dried (Na2SO4), filtered, and concentrated to provide the crude title compound as a clear yellow oil.

Provenance & Evidence