1,2-Dimethoxyethane → 2-Bromo-6-phenylnaphthalene

Participants

Reaction Conditions

Reaction Steps

Under an argon gas atmosphere, 128.0 g (1.049 mol) of phenylboronic acid, 300.0 g (1.163 mol) of 2,6-dibromonaphthalene, 24.2 g (21.0 mmol) of tetrakis(triphenylphosphine)palladium(0), 4.3 L of dimethoxyethane and 1.60 L of aqueous solution of 2M sodium carbonate were added together, and stirred at 78 degrees C. for 24 hours. The reaction mixture was added with toluene and water, and aqueous phase thereof was eliminated. After organic phase thereof was washed by water and dried with magnesium sulfate, the toluene was distilled away under reduced pressure. Residue thereof was refined by silica-gel column chromatography and recrystallized with hexane such that 108 g of 2-bromo-6-phenylnaphthalene was obtained at an yield of 36%.

Provenance & Evidence