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

Temperature

155 °C

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.

1. customwas degassed for 30 minutes
2. temperatureAfter cooling
3. additionthe resulting 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

ORD record

ord-0a9f630621ff4a4eabeb961d766afbf9

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08771845B2