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

HRID 1618829Notes

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

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 resulting mixture was then heated to about 155° C. for 66 hours under argon. After cooling, the resulting 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; confirmed by HNMR.

Workup

customwas degassed for 30 minutes
temperatureAfter cooling
additionthe resulting mixture was poured into methylene chloride (400 mL)
filtrationthe subsequent mixture was filtered
customA flash column (silica, 10% methylene chloride in hexane) and reprecipitation in methylene chloride/hexanes

Sources & evidence

ORD record: ord-0a9f630621ff4a4eabeb961d766afbf9
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08771845B2

Reaction notes

Loading…