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

HRID 1037506Notes

Reaction equation

HRID 1037506 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

5

Reactant 4

HCID 962WaterHCID 10486tert-BUTYL CHLORIDEHCID 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%).

Workup

  1. waitdisappeared within minutes
  2. customof reacting at room temperature
  3. waitThe reaction was carried out at room temperature for another 10 minutes
  4. filtrationThe solid product was collected with filtration
  5. washwashed with methanol
  6. customThe product was purified by recrystallization from acetone/THF/methanol
  7. customto yield a white solid in the amount of 1.23 g (79.4%)

Sources & evidence

ORD record
ord-4df7734bacbf40279c98f0f3180ba066
Source dataset
uspto-grants-2013_10
Patent number
US08546505B2

Reaction notes

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