Water → Benzyl trifluoromethyl sulfide
Reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:9][C:10]([F:13])([F:12])[S-:11].CN([S+](N(C)C)N(C)C)C.O>C(#N)C>[F:9][C:10]([S:11][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([F:13])[F:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Benzyl bromide, 16.2 g (0.095 mol), was added dropwise at 25° to 0.11 mol of tris(dimethylamino)sulfonium trifluoromethanethiolate (prepared as in Example 11) in 75 mL of acetonitrile. The reaction mixture was stirred one 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 15.1 g (82%) of benzyl trifluoromethyl sulfide as a colorless liquid: bp 55° (12 mm); 1H NMR (CDCl3) δ4.08 ppm (s, 2H), 7.33 ppm (s, 5H); 19F NMR (CDCl3) δ-42.5 ppm (s).