1,2-Dimethoxyethane → 6-Bromo-2-(9-phenanthrenyl)naphthalene

Participants

Reaction Conditions

Reaction Steps

In argon atmosphere, a mixture of 15.53 g (69.6 mmol) of 9-phenanthreneboronic acid, 20.00 g (69.9 mmol) of 2,6-dibromonaphthalene, 1.62 g (1.40 mmol) of tetrakis(triphenylphosphine)palladium (0), 150 ml of dimethoxyethane, 150 ml of toluene, and 106 g of a 2 M sodium carbonate aqueous solution was stirred at a bath temperature of 85° C. for 7 h. The reaction mixture was added with water and extracted with toluene. After washing with water, the organic phase was dried over magnesium sulfate. Then the toluene was removed by distillation under reduced pressure. The residue was purified by silica gel chromatography to obtain 11.6 g (yield: 43%) of 6-bromo-2-(9-phenanthrenyl)naphthalene.

Provenance & Evidence