Carbazole → 4,4'-Bis(9H-carbazol-9-yl)biphenyl

HRID 661812Notes

Reaction equation

HRID 661812 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11](I)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH:15]1[C:27]2[NH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]=2[CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].C([C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([CH:43]([CH3:45])[CH3:44])[CH:38]=1)(C)C>[Cu].C1(C)C=CC=CC=1>[CH:3]1[C:4]2[N:26]([C:25]3[CH:20]=[CH:44][C:43]([C:39]4[CH:38]=[CH:37][C:42]([N:26]5[C:25]6[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=6[C:19]6[C:27]5=[CH:15][CH:16]=[CH:17][CH:18]=6)=[CH:41][CH:40]=4)=[CH:45][CH:24]=3)[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:5]=2[CH:6]=[CH:7][CH:2]=1

Participants

7

Reactant 4

HCID 6854CarbazoleHCID 74501,3-DiisopropylbenzeneHCID 11430Potassium CarbonateHCID 763484,4'-Diiodo-1,1'-biphenyl

Product 1

HCID 112487164,4'-Bis(9H-carbazol-9-yl)biphenylYield 68.6%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 1140TolueneSolvent

Procedure

A 2-L Kolben equipped with a stirrer and a drain device was charged under a nitrogen stream with 150 g (369.5 mmol) of 4,4′-diiodobiphenyl, 123.5 g (738.6 mmol) of carbazole, 23 g of copper powder, 100 g of potassium carbonate, and 500 ml of 1,3-diisopropylbenzene. The mixture was heated under reflux for 30 hr and was allowed to cool. Toluene was then added, and the mixture was filtered. The solvent in the filtrate was distilled off under reduced pressure. Methanol (500 ml) was added to the residue to precipitate crystals. The crystals were collected by filtration to give CBP (4,4′-bis(carbazol-9-yl)-biphenyl) (122.8 g, yield 68.6%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 30 hr
  3. temperatureto cool
  4. filtrationthe mixture was filtered
  5. distillationThe solvent in the filtrate was distilled off under reduced pressure
  6. additionMethanol (500 ml) was added to the residue
  7. customto precipitate crystals
  8. filtrationThe crystals were collected by filtration

Sources & evidence

ORD record
ord-fcbc2aaf753643d6aa7d9fc0c3acceb3
Source dataset
uspto-grants-2011_12
Patent number
US08084935B2

Reaction notes

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