Toluene → 5-(3-Bromophenyl)benzo[c]phenanthrene

Participants

Reaction Steps

In argon atmosphere, a mixture of 6.32 g (22.3 mmol) of 5-benzo[c]phenanthreneboronic acid, 5.07 g (18.6 mmol) of 3-bromoiodobenzene, 1.29 g (1.12 mmol) of tetrakis(triphenylphosphine)palladium (0), 80 ml of toluene, 80 ml of dimethoxyethane, and 33.8 g of a 2 M sodium carbonate aqueous solution was refluxed for 8 h under stirring. After the reaction, the reaction mixture was added with water and extracted with toluene. The organic phase was washed with water and dried over sodium sulfate, and then the toluene was removed by distillation under reduced pressure. The residue was purified by silica gel chromatography to obtain 4.53 g (yield: 56.8%) of 5-(3-bromophenyl)benzo[c]phenanthrene.

Provenance & Evidence