Reaction #1509642

Reaction equation

carbazole

4,4′-dibromobiphenyl

18-crown-6

potassium carbonate

→

pure product

Yield 42.2%

9-(4′-bromobiphenyl-4-yl)-9H-carbazole

Yield 42.2%

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   Otherwas degassed for 30 minutes
2. 2
   TemperatureAfter cooling
3. 3
   workup.ADDITIONthe resulting mixture was poured into methylene chloride (400 mL)
4. 4
   Filtrationthe subsequent mixture was filtered
5. 5
   OtherA flash column (silica, 10% methylene chloride in hexane) and reprecipitation in methylene chloride/hexanes

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.

Source