Water → 1,3-Bis(3,6-di-tert-butylcarbazol-9-yl)benzene

Reaction equation

[CH:1]1[C:13]2[N:12]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([N:20]4[C:32]5[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=5[C:26]5[C:21]4=[CH:22][CH:23]=[CH:24][CH:25]=5)[CH:15]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Cl-].[Cl-].[Cl-].[Al+3].O.Cl[C:39]([CH3:42])([CH3:41])[CH3:40]>>[C:39]([C:8]1[CH:9]=[CH:10][C:11]2[N:12]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([N:20]4[C:21]5[CH:22]=[CH:23][C:24]([C:5]([CH3:6])([CH3:13])[CH3:4])=[CH:25][C:26]=5[C:27]5[C:32]4=[CH:31][CH:30]=[C:29]([C:26]([CH3:27])([CH3:21])[CH3:25])[CH:28]=5)[CH:15]=3)[C:13]3[C:5]([C:6]=2[CH:7]=1)=[CH:4][C:3]([C:39]([CH3:42])([CH3:41])[CH3:40])=[CH:2][CH:1]=3)([CH3:42])([CH3:41])[CH3:40]

Participants

Reactant 4

HCID 962Water

HCID 10486tert-BUTYL CHLORIDE

HCID 6451240Aluminum(III) Chloride2×

HCID 220203771,3-Bis(N-carbazolyl)benzene2×

Product 1

HCID 597755151,3-Bis(3,6-di-tert-butylcarbazol-9-yl)benzene

Procedure

To a solution of 1,3-di(carbazol-9-yl)benzene (1.0 g, 2.45 mmol) in 2-chloro-2-methylpropane (10.0 ml) was added aluminum trichloride (0.32 g, 2.40 mmol) at room temperature under nitrogen atmosphere and stirring. After the addition of AlCl3, insoluble 1,3-di(carbazol-9-yl)benzene disappeared within minutes. The green solid appeared after 5 minutes of reacting at room temperature. The reaction was carried out at room temperature for another 10 minutes. TLC showed that the reaction was finished. After which, water (20.0 ml) was added and the green solid became white. The solid product was collected with filtration and washed with methanol. The product was purified by recrystallization from acetone/THF/methanol to yield a white solid in the amount of 1.23 g (79.4%).