Reaction #2460315

Reaction equation

methyl trifluoromethanesulfonate

Trans-4,4′-di[(4-n-butylphenyl)(3-benzylthiophenyl)amino]stilbene

→

trans-[3-((4-butylphenyl){4-[2-(4-{(4-butylphenyl)[3-((benzyl) methylsulfonio)phenyl]amino}phenyl)vinyl]phenyl}amino)phenyl]((benzyl)methyl)sulfonium triflate

Solvents

dry ice acetone

methylene chloride

Conditions

Workup

1. 1
   workup.ADDITIONTo this solution was added, via syringe
2. 2
   OtherAfter removal of some solvent under reduced pressure
3. 3
   workup.ADDITIONthe mixture was then poured into 20 ml of ether
4. 4
   OtherThe product was precipitated as a yellow solid, that
5. 5
   Washwas washed three times with ether
6. 6
   Otherisolated in 80.9% (1.07 g)
7. 7
   Otheryield

Procedure

Trans-4,4′-di[(4-n-butylphenyl)(3-benzylthiophenyl)amino]stilbene (16) (0.96 g, 1.103 mmol) was dissolved in 20 ml of dry methylene chloride and cooled at −78° C. in dry ice-acetone bath. To this solution was added, via syringe, methyl trifluoromethanesulfonate (276 μl, 2.437 mmol) and the mixture stirred for 30 min while the temperature was maintained at −78° C. The resultant mixture was then stirred two days at room temperature. After removal of some solvent under reduced pressure, the mixture was then poured into 20 ml of ether. The product was precipitated as a yellow solid, that was washed three times with ether and isolated in 80.9% (1.07 g) yield. 1H NMR (CD3COCD3, 500 MHz) δ ppm: 6.9-7.8 (m, 34 Ar—H, 2 ═CH), 5.27 (d, 2J=12.5 Hz, 2H, SCH2), 5.02 (d, 2J=12.5 Hz, 2H, SCH2), 3.53 (s, 6H, CH3), 2.63 (t, J=7.7 Hz, CH2, 4H), 1.61 (m, CH2, 4H), 1.36 (m, CH2, 4H), 0.95 (t, J=7.2 Hz, CH3, 6H)13C NMR (CD3COCD3, 125.7 MHz) δppm: 149.4, 145.6, 143.6, 139.9, 133.5, 131.8, 130.7, 130.1, 129.8, 129.3, 127.9, 127.7, 127.1, 126.5, 125.7, 124.5, 123.8, 123.4, 121.7, 51.0, 34.7, 33.5, 24.5, 22.1, 13.3. (One CF3 carbon was not observed).

Source