Carbazole → 9-(4'-Bromo-4-biphenylyl)carbazole

HRID 1618825Notes

Reaction equation

HRID 1618825 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Br:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24](Br)=[CH:23][CH:22]=2)=[CH:17][CH:16]=1.C1OCCOCCOCCOCCOCCOC1.C(=O)([O-])[O-].[K+].[K+]>[Cu].CN(C)C=O>[Br:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[CH:26]=[CH:25][C:24]([N:12]3[C:11]4[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=4[C:5]4[C:13]3=[CH:1][CH:2]=[CH:3][CH:4]=4)=[CH:23][CH:22]=2)=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 6854CarbazoleHCID 71104,4'-DibromobiphenylHCID 11430Potassium CarbonateHCID 2855718-Crown-6

Product 1

HCID 588923869-(4'-Bromo-4-biphenylyl)carbazoleYield 42.2%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
155 °C

Procedure

A mixture of carbazole (300 mg, 1.81 mmol), 4,4′-dibromobiphenyl (846 mg, 2.71 mmol), copper (344 mg, 5.43 mmol), 18-crown-6 (187 mg, 0.71 mmol), potassium carbonate (750 mg, 5.43 mmol), and anhydrous N,N-dimethylformamide (10 mL) was degassed for 30 minutes. The mixture was heated to 155° C. for 66 hours under argon. After cooling, the mixture was poured into DCM (400 mL) and the subsequent mixture was filtered. The filtrate was loaded on silica gel. A flash column (silica, 10% DCM in hexane) and reprecipitation in DCM/hexanes yielded 304 mg (42% yield) of pure product; confirmed by HNMR.

Workup

  1. customwas degassed for 30 minutes
  2. temperatureAfter cooling
  3. additionthe mixture was poured into DCM (400 mL)
  4. filtrationthe subsequent mixture was filtered
  5. customA flash column (silica, 10% DCM in hexane) and reprecipitation in DCM/hexanes

Sources & evidence

ORD record
ord-298ef4af004449d288580871ea0d4413
Source dataset
uspto-grants-2014_07
Patent number
US08771845B2

Reaction notes

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