Hypofluorous acid, trifluoromethyl ester → 2-Fluoro-1,2-diphenylethan-1-one

Participants

Reaction Steps

A solution of 18.8 g (0.07 mol) of the aforesaid α-trimethylsiloxystilbene in 200 ml of chlorotrifluoromethane was cooled to -70° C. and 7.3 g (0.07 mol) of trifluoromethyl hypofluorite were passed into the solution over a 3 hour period. The reaction mixture then was warmed to room temperature and evaporated to dryness under reduced pressure to give a white solid. Recrystallization from heptane gave 10.81 g (72% yield) of α-fluoro-α-phenylacetophenone as colorless crystals: mp 50°-51° C.; 19F NMR (CDCl3) δ-176.5 ppm (d, J=49 Hz); 1H NMR (CDCl3) δ 6.52 ppm (d, J=49 Hz, 1H), 7.2-8.2 ppm (m, 10H). Anal. Calcd. for C14H11FO: C, 78.49; H, 5.18; F, 8.87; Found: C, 78.52; H, 5.13; F, 8.65.

Provenance & Evidence