Reaction #1516508

Reaction equation

9-phenanthreneboronic acid

2,6-dibromonaphthalene

dimethoxyethane

sodium carbonate

→

6-bromo-2-(9-phenanthrenyl)naphthalene

Yield 43.5%

Solvents

water

toluene

Conditions

Workup

1. 1
   Extractionextracted with toluene
2. 2
   WashAfter washing with water
3. 3
   Dryingthe organic phase was dried over magnesium sulfate
4. 4
   OtherThen the toluene was removed by distillation under reduced pressure
5. 5
   OtherThe residue was purified by silica gel chromatography

Procedure

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.

Source