Reaction #2460316

Reaction equation

trans-{3-[[4-(2-{4-[[3-(dimethylsulfonio)phenyl](phenyl)amino]phenyl}vinyl)phenyl](phenyl)amino]phenl}(dimethyl)sulfonium triflate

{3-[[4-(2-{4-[[3-(dimethylsulfonio)phenyl](phenyl)amino]-phenyl}-vinyl)phenyl](phenyl)amino]phenyl}(dimethyl)sulfonium triflate

sodium hexafluoroantimonate

→

{3-[[4-(2-{4-[[3-(dimethylsulfonio)phenyl](phenyl)amino]phenyl}vinyl)phenyl](phenyl)amino]phenyl}(dimethyl)sulfonium hexafluoro-antimonate

Solvents

methylene chloride

acetone

Conditions

Workup

1. 1
   Otherwith slow evaporation of methylene chloride and acetone
2. 2
   Othera yellow solid was formed
3. 3
   Filtrationcollected by filtration
4. 4
   WashThe yellow solid was washed four times with water and three times with ether
5. 5
   OtherNMR-pure product was obtained without further purification in 75.4% (0.31 g)
6. 6
   Otheryield

Procedure

trans-{3-[[4-(2-{4-[[3-(dimethylsulfonio)phenyl](phenyl)amino]phenyl}vinyl)phenyl](phenyl)amino]phenl}(dimethyl)sulfonium triflate (17) (0.3 g 0.33 mmol) was dissolved in methylene chloride (5 ml) and acetone (10 ml). To this solution was added 10 ml aqueous sodium hexafluoroantimonate solution (0.341 g, 1.32 mmol). The resultant mixture was stirred three days in the dark at room temperature with slow evaporation of methylene chloride and acetone, a yellow solid was formed and collected by filtration. The yellow solid was washed four times with water and three times with ether. NMR-pure product was obtained without further purification in 75.4% (0.31 g) yield. 1H NMR (DMSO, 500 MHz) δ ppm: 7.0-7.6 (m, 26H, Ar—H), 7.16 (s, ═CH, 2H), 3.35 (s, CH3, 12H) Anal. calcd for C44H40N2S2Sb2F12: C, 45.51; H, 3.64; N, 2.53; S, 5.78.

Source