Benzyl Bromide → HCID 13765565, compound

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Reaction Steps

Benzyl bromide, 12.47 g (0.073 mol), was added dropwise at 25° to a solution of 0.081 mol of tris(dimethylamino)sulfonium trifluoromethoxide (prepared as in Example 1) in 75 mL of acetonitrile. The reaction mixture was stirred at 25° for 18 h 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 10.55 g (85%) of benzyl trifluoromethyl ether as a colorless oil: bp 45°-46° (18 mm); 1H NMR (CDCl3) δ4.93 ppm (s, 2H), 7.33 ppm (s, 5H); 19F NMR (CDCl3) δ-60.6 ppm (s). Anal. Calcd. for C8H7F3O: C, 54.55; H, 4.01; F, 32.36. Found: C, 54.76; H, 4.04; F, 32.51.

Provenance & Evidence