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

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.

1. customprepared
2. temperatureThe reaction mixture was warmed to 25°
3. extractionThe aqueous mixture was extracted with ether
4. washthe ether extracts were washed three times with water
5. dry with materialdried (MgSO4)
6. distillationdistilled

ORD record

ord-7e9982878cec40cfa307d5aa99eb747e

Source dataset

uspto-grants-1985_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04535184