Carbazole → 9-(4-Bromophenyl)carbazole

Participants

Reaction Conditions

Reaction Steps

Compound 4 was prepared as follows: a mixture of carbazole (6.30 g, 37.7 mmol), 1-bromo-4-iodobenzene (15.99 g, 56.52 mmol), copper powder (4.79 g, 75.4 mmol), K2CO3 (20.83 g, 150.7 mmol) and anhydrous DMF (100 mL) was degassed with argon for about 1 h while stirring. The stirring reaction mixture was then maintained under argon at about 130° C. for about 42 h. Upon confirming consumption of the starting material by TLC (SiO2, 4:1 hexanes-dichloromethane), the mixture was cooled to RT, filtered, the filtrant washed copiously with EtOAc (ca. 200 mL) and the resulting filtrate concentrated in vacuo. Purification of the crude product by flash chromatography (SiO2, hexanes) afforded compound 4 (11.7 g, 96% yield) as a pale yellow solid. (See Xu, H.; Yin, K.; Huang, W. Chem. Eur. J., 2007, 13(36), 10281-10293.)

Provenance & Evidence