Reaction #2460329

Reaction equation

4-[2-(4-bromophenyl)vinyl]-N, N-bis(4-butylphenyl)aniline

Sodium tert-butoxide

phenothiazine

water

→

N,N-bis(4butylphenyl)-N-(4-{2[4-(10H-phenothiazin-10-yl)phenyl]vinyl}phenyl)amine

Solvents

toluene

Conditions

Workup

1. 1
   Extractionextracted three times with ether (100 ml×3)
2. 2
   Dryingdried over anhydrous magnesium sulfate
3. 3
   OtherThe product was purified by flash column chromatography
4. 4
   Otherwas isolated in 60% (1.91 g)
5. 5
   Otheryield as a yellow solid

Procedure

To a solution of tris(dibenzylideneacetone) dipalladium (Pd2(dba)3) (0.13 g, 0.14 mmol) and bis(diphenylphosphino)ferrocene (DPPF) (0.10 g, 0.17 mmol) in dry toluene (20 ml) under nitrogen atmosphere was added 4-[2-(4-bromophenyl)vinyl]-N, N-bis(4-butylphenyl)aniline (2.60 g, 4.83 mmol) at room temperature, and the resultant mixture was stirred for 10 min. Sodium tert-butoxide (1.3 g) and phenothiazine (0.96 g, 4.83 mmol) were then added to this solution, which was then stirred at 90° C. overnight under nitrogen. The reaction mixture was poured into water (60 ml), extracted three times with ether (100 ml×3) and dried over anhydrous magnesium sulfate. The product was purified by flash column chromatography using 2% ethyl acetate in hexane as eluant and was isolated in 60% (1.91 g) yield as a yellow solid.

Source