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

HRID 2206839Notes

Reaction equation

HRID 2206839 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]>[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

6

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 1

HCID 23978CopperCatalyst

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-dimethylformnamide (10 ml) was degassed for 30 minutes. The mixture was heated at about 155° C. for 66 hours under argon. After being cooled to RT, the mixture was poured into methylene chloride (400 ml) and the subsequent mixture was filtered. The filtrate was loaded on silica gel. A flash column (silica, 10% methylene chloride in hexane) and reprecipitation in methylene chloride/hexanes yielded 304 mg (42% yield) of pure product 10; confirmed by HNMR

Workup

  1. customwas degassed for 30 minutes
  2. temperatureAfter being cooled to RT
  3. additionthe mixture was poured into methylene chloride (400 ml)
  4. filtrationthe subsequent mixture was filtered
  5. customA flash column (silica, 10% methylene chloride in hexane) and reprecipitation in methylene chloride/hexanes

Sources & evidence

ORD record
ord-41c025754d0949e382fddd2b56a876f7
Source dataset
uspto-grants-2016_06
Patent number
US09373797B2

Reaction notes

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