General method: 3,6-di-tert-butylcarbazole (0.5 mmol) and p-bromofluorobenzene (2.0 mmol) were mixed in a solvent (2 mL) in the presence of a base (2.0 mmol). The reaction mixture was heated to the indicated temperature under air atmosphere for 24 hours. Upon completion of the reaction, the mixture was poured into brine (15 mL) and extracted with dichloromethane (3 x 15 mL). The organic phases were combined, concentrated under reduced pressure and the target product 9-(4-bromophenyl)-3,6-di-tert-butyl-9H-carbazole was isolated and purified by chromatography on a 200-300 mesh silica gel column.
