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

HRID 1968382
Notes
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Reaction equation

HRID 1968382 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 23978
Copper
Catalyst
HCID 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 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-996690afcc394b7794d45b47536b8389
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08426040B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes