Toluene → 2-bromo-9,9-dimethyl-7-(naphthalene-2-yl)-9H-fluorene

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Reaction Steps

In argon atmosphere, a mixture of 13.91 g (80.9 mmol) of 2-naphthaleneboronic acid, 30.0 g (80.9 mmol) of 2-bromo-7-iodo-9,9-dimethylfluorene, 4.67 g (4.0 mmol) of tetrakis(triphenylphosphine)palladium (0), 200 ml of toluene, 200 ml of dimethoxyethane, and 122.36 g of a 2 M sodium carbonate aqueous solution was refluxed under stirring for 8 h and left standing overnight. After adding water, the mixture was stirred at room temperature for one hour. After filtration and extraction with toluene, the organic phase was washed with water and then with a saturated saline solution. After drying over sodium sulfate, the toluene was distilled off under reduced pressure. The residue was purified by silica gel chromatography to obtain 21.3 g (yield: 76.1%) of 2-bromo-9,9-dimethyl-7-(naphthalene-2-yl)-9H-fluorene.

Provenance & Evidence