Reaction #2460314

Reaction equation

sodium tert-butoxide

4-n-butyl aniline

trans-4,4′-dibromostilbene

→

trans-4,4′-di(p-n-butylphenyl)aminostilbene

Solvents

toluene

Conditions

Workup

1. 1
   OtherThe solid was collected
2. 2
   Washwashed three times with methanol and ether
3. 3
   Otherisolated in 68.8% (1.93 g)
4. 4
   Otheryield as an NAM-pure product

Procedure

To a solution of tris(di-benzylideneacetone)dipalladium (Pd2(dba)3) (0.335 g, 0.365 mmol) and bis-(diphenylphosphino)ferrocene (DPPF) (0.294 g, 0.530 mmol) in dry toluene (20 ml) under nitrogen atmosphere was added trans-4,4′-dibromostilbene (10) (2.0 g, 5.91 mmol) at room temperature, and the resultant mixture was stirred for 10 min, sodium tert-butoxide (2.6 g) and 4-n-butyl aniline (1.77 g, 11.83 mmol) were added to this solution and stirred at 90° C. overnight. The solid was collected, washed three times with methanol and ether, and isolated in 68.8% (1.93 g) yield as an NAM-pure product. 1H NMR (CDCl3, 500 MHz) δ ppm: 7.38 (d, J=8.0 Hz, 4H), 7.10 (d, J=8.5 Hz, 4H), 7.03 (d, J=8.0 Hz, 4H), 7.0 (d, J=8.5 Hz, 4H), 6.91 (s, 2H, ═CH), 5.77 (s, 2H, NH), 2.56 (t, J=7.7 Hz, CH2, 4H), 1.59 (m, CH2, 4H), 1.37 (m, CH2, 4H), 0.94 (t, J=7.5Hz, CH3, 6H).

Source