Carbazole → 1,3-Bis(N-carbazolyl)benzene

HRID 1037509Notes

Reaction equation

HRID 1037509 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[C:4](I)[CH:3]=1.[CH:9]1[C:21]2[NH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]=2[CH:12]=[CH:11][CH:10]=1.C1O[CH2:38][CH2:37]OCCOCCOCCOCCOC1.C(=O)([O-])[O-].[K+].[K+]>ClC1C=CC=CC=1Cl>[CH:2]1[C:3]2[N:20]([C:38]3[CH:37]=[CH:21][CH:9]=[C:10]([N:20]4[C:19]5[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=5[C:13]5[C:21]4=[CH:9][CH:10]=[CH:11][CH:12]=5)[CH:11]=3)[C:19]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6854CarbazoleHCID 11430Potassium CarbonateHCID 12270Benzene, 1,3-diiodo-HCID 2855718-Crown-6

Product 1

HCID 220203771,3-Bis(N-carbazolyl)benzene

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

To a solution of 1,3-diiodobenzene (50.0 g, 0.152 mol), carbazole (55.0 g, 0.329 mol), Cu (40.0 g, 0.630 mol) and 18-crown-6 (0.5 g) in 1,2-dichlorobenzene (200.0 ml) was added potassium carbonate (150.0 g, 1.085 mol) under nitrogen and stirring. The reaction was carried out at 190° C. for 12 hours. After cooling, the reaction mixture was filtrated. The solid residues were carefully washed with THF. Then, THF and 1,2-dichlorobenzene were evaporated from the combined filtration solution. The crude product was purified by recrystallization from acetone/methanol to give 47.0 g (75.7%) in yield.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtrated
  3. washThe solid residues were carefully washed with THF
  4. customThen, THF and 1,2-dichlorobenzene were evaporated from the combined filtration solution
  5. customThe crude product was purified by recrystallization from acetone/methanol
  6. customto give 47.0 g (75.7%)
  7. customin yield

Sources & evidence

ORD record
ord-d4c66e6e4da54063a83a6b554a01f228
Source dataset
uspto-grants-2013_10
Patent number
US08546505B2

Reaction notes

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