Water → HCID 13765570, compound

Participants

Reaction Steps

Benzyl bromide, 10.62 g (0.0621 mol), was added dropwise to a solution of 27.5 g (0.069 mol) of tris(dimethylamino)sulfonium 1,1,2,3,3,3-hexafluoro-2-(trifluoromethyl)propoxide (prepared as in Example 7) in 50 mL of acetonitrile at 25°. The reaction mixture was stirred for 2 h and then poured into water. The aqueous mixture was extracted with ether, and the ether extracts were washed with water, dried (MgSO4), and distilled to give benzyl 1,1,2,3,3,3-hexafluoro-2-(trifluoromethyl)propyl ether as a colorless liquid: bp 86°-87° (36 mm); 19F NMR (CDCl3) δ-73.9 ppm (t, d, J=9, 6 Hz, 6F), -79.2 ppm (d, septet, J=9, 9 Hz, 2F), and -187.7 ppm (t, septet, J=9, 6 Hz, 1F). Anal. Calcd. for C11H7F9O: C, 40.50; H, 2.16. Found: C, 40.69; H, 2.29.

Provenance & Evidence