Dimethyl Ether → 1-Bromo-4-(2-formylphenyl)naphthalene

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Reaction Steps

Under an argon atmosphere, 230 g of 1,4-dibromonaphthalene, 121 g of 2-formylphenylboronic acid and 18.5 g of tetraxis(triphenylphosphine)palladium(0) were placed in a flask. 2.4 L of dimethyl ether (DME) and 1.2 L of a 2M aqueous sodium carbonate solution were added to this flask, and the resultant was refluxed with stirring while heating for 8 hours. After cooling to room temperature, an aqueous phase was removed. An organic phase which had been separated was washed with water, and saturated brine, and then dried with magnesium sulfate. After the magnesium sulfate was filtered out, the organic phase was concentrated. The resulting residue was purified by means of silica gel column chromatography, whereby 170 g (yield: 67%) of 1-bromo-4-(2-formylphenyl) naphthalene was obtained.

Provenance & Evidence