Toluene → 4-broMo-9-phenyl-9H-carbazole

Participants

Reaction Conditions

Reaction Steps

A reaction vessel was charged with 4.37 mmol (4.00 g) Pd2dba3, (dba=dibenzoylacetone), 6.55 mmol (3.63 g) dppf (dppf=diphenylphosphine ferrocene), and 400 ml dry toluene. Using a magnetic stir bar and hot plate, the mixture was stirred for 15 minutes under argon. Then 436 mmol (48.92 g) sodium t-butoxide was added against counter flow of argon and the reaction was stirred another 30 minutes. Then 291 mmol (48.66 g) carbazole with 873 mmol (205.96 g) 1,4-dibromobenzene were added and the reaction was heated to 100° C. for 16 hours. The reaction progress was followed by TLC until no carbazole could be detected. At end of reaction, the reaction mixture was taken up into water/ether (2:1). The mixture was then washed with water until the organic layer was colorless, then the solution was concentrated. The residue was dissolved in a mixture of toluene/hexane and passed through a short column of silica gel. The solvent was then removed from the column filtrate which yielded the product.

Provenance & Evidence