Hypofluorous acid, trifluoromethyl ester → HCID 4111754, compound

Participants

Reaction Steps

A solution of 3.0 g (0.0127 mol) of β-(N,N-dimethylamino)-β-(trimethylsiloxy)styrene (from above) in 100 ml of chlorotrifluoromethane was cooled to -70° C. and 1.6 g (0.013 mol) of trifluoromethyl hypofluorite were passed into the solution over a period of 3 hours. The reaction mixture was warmed to room temperature and then distilled to give 1.49 g (65% yield) of α-fluoro-N,N-dimethylbenzeneacetamide as a colorless oil: bp 98°-100° C. (0.45 mm); 19F NMR (CCl3F) δ-175.9 ppm (d,J=50 Hz); 1H NMR (CCl3F) δ 2.86 ppm (s, 6H), 5.54 ppm (d,J=50 Hz, 1H) and 7.10-7.8 ppm (m, 5H). Anal. Calcd for C10H12FNO: C, 66.27; H, 6.68; F, 10.49; N, 7.73; Found: C, 66.41; H, 6.75; F, 10.30; N, 7.70.

Provenance & Evidence