Benzyl Bromide → HCID 12710434, compound

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Reaction Steps

Benzyl bromide, 16.76 g (0.098 mol), was added dropwise at 25° to a solution of 0.098 mole of tris(dimethylamino)sulfonium 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethanethiolate (prepared as in Example 12) in 125 mL of acetonitrile. The reaction mixture was stirred for 18 h and then poured into 500 mL of ice-water. The aqueous mixture was extracted with ether, and the ether extracts were washed with water, dried (MgSO4) and distilled to give 21.31 g (75% yield) of benzyl heptafluoroisopropyl sulfide as a pale yellow liquid: bp 70°-71° (10 mm); 1H NMR (CDCl3) δ4.09 ppm (s, 2H) and 7.27 ppm (s, 5H); 19F NMR (CDCl3) δ-75.2 ppm (d, J=11 Hz, 6F) and -162.6 ppm (septet, J=11 Hz, 1F). Anal. Calcd. for C10H7F7S: C, 41.10; H, 2.41; F, 45.51. Found: C, 40.89; H, 2.45; F, 45.27.

Provenance & Evidence