Phenacyl bromide → 1-phenyl-2-(trifluoromethoxy)ethan-1-one

Participants

Reaction Steps

α-Bromoacetophenone, 13.61 g (0.068 mol), was added dropwise at 25° to a solution of 0.076 mol of tris(dimethylamino)sulfonium trifluoromethoxide (prepared as in Example 1) in 75 mL of acetonitrile. The reaction mixture was stirred for 3 days and then poured into ice-water. The aqueous mixture was extracted with ether, and the ether extracts were washed with water, dried (MgSO4), and distilled to give α-trifluoromethoxyacetophenone as a colorless liquid: bp 64°-65° (0.8 mm); 1H NMR (CDCl3) δ5.15 ppm (s, 2H), 7.50 ppm (m, 3H), 7.85 ppm (m, 2H); 19F NMR (CDCl3) δ-61.5 ppm(s).

Provenance & Evidence