Benzyl Bromide → [2,2-Bis(trifluoromethyl)-3,3,3-trifluoropropyl]benzene

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Reaction Steps

Benzyl bromide, 18.8 g (0.11 mol), was added dropwise at 10° to a solution of tris(dimethylamino)sulfonium 1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)-2-propanide, prepared by dissolving 24.4 g (0.122 mol) of octafluoroisobutylene and 33.6 g (0.122 mol) of tris(dimethylamino)sulfonium difluorotrimethylsilicate in 75 mL of acetonitrile. The reaction mixture was warmed to 25°, stirred overnight, and then poured into ice water. The aqueous mixture was extracted with ether, and the ether extracts were washed three times with water, dried (MgSO4), and distilled to give 27.35 g (81%) of 3,3,3-trifluoro-2,2-bis(trifluoromethyl)propylbenzene as a colorless liquid, b.p. 53°-54° (12 mm), that solidified on cooling to a white solid: m.p. 32°-33°; 1H NMR (CDCl3) δ 3.39 ppm (s, 2H), 7.28 ppm (s, 5H); 19F NMR (CDCl3) δ -62.3 ppm (s). Anal. Calcd. for C11H7F9 : C, 42.59; H, 2.28; F, 55.13. Found: C, 42.45; H, 2.23; F, 55.00.

Provenance & Evidence