Toluene → 2-(6-bromonaphthalene-2-yl)-9,9-dimethyl-9H-fluorene

Participants

Reaction Conditions

Reaction Steps

16.65 g (69.9 mmol) of 9,9-dimethyl-9H-fluorene-2-ylboronic acid, 20.0 g (69.9 mmol) of 2,6-dibromonaphthalene, 4.04 g (3.50 mmol) of tetrakis(triphenylphosphine)palladium (0), 200 ml of toluene, 200 ml of dimethoxyethane and 106 g of a 2M sodium carbonate aqueous solution were combined under argon atmosphere, and the mixture was stirred at 85° C. for 8 hours and left standing overnight. Water was added to the reaction mixture, and the mixture was stirred at room temperature for one hour. The mixture was filtered, the filtrate was extracted with toluene, and the organic phase was washed with water and subsequently with a saturated saline solution. The liquid was dried on sodium sulfate, and then toluene was removed by distillation under reduced pressure. A brown oily substance which resulted was refined by silica gel chromatography to obtain 11.8 g (yield: 42.4%) of 2-(6-bromonaphthalene-2-yl)-9,9-dimethyl-9H-fluorene.

Provenance & Evidence