Reaction #2460317

Reaction equation

sodium hexafluoroantimonate

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

→

[3-((4-butylphenyl){4-[2-(4-{(4-butylphenyl)[3-(dimethyl-sulfonio)phenyl]amino}phenyl)vinyl]phenyl}amino)phenyl](dimethyl)sulfonium hexafluoroantimonate

Solvents

acetone

Conditions

Workup

1. 1
   Otherwith slow evaporation of 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
   OtherA NMR-pure product was obtained without further purification
6. 6
   Otherisolated in 93.8% (0.95 g)
7. 7
   Otheryield

Procedure

Trans-[3-((4-butylphenyl){4-[2-(4- {(4-butylphenyl)[3-(dimethylsulfonio)phenyl]amino}phenyl)vinyl]phenyl}amino)phenyl](dimethyl)sulfonium triflate (19) (0.87 g, 0.83 mmol) was dissolved in acetone (20 ml). To this solution was added 20 ml of an aqueous solution of sodium hexafluoroantimonate (0.88 g, 3.40 mmol). The resultant mixture was stirred two days in the dark at room temperature; with slow evaporation of acetone, a yellow solid was formed and collected by filtration. The yellow solid was washed four times with water and three times with ether. A NMR-pure product was obtained without further purification and isolated in 93.8% (0.95 g) yield. 1H NMR (CD3COCD3, 500 MHz) δ ppm: 7.1-7.4 (m, 24 Ar—H, 2 ═CH), 3.06 (s, 6H, CH3,) 2.72 (t, J=7.7 Hz, CH2, 4H), 1.71 (m, CH2, 4H), 1.46 (m, CH2, 4H), 1.04 (t, J=7.3 Hz, CH3, 6H)

Source