Tetrahydrofuran → 1-Bromo-4-[1-(2-methoxyvinyl)phenyl]naphthalene

Participants

Reaction Steps

Under an argon atmosphere, 170 g of the resulting 1-bromo-4-(2-formylphenyl)naphthalene, 207 g of methoxymethyl triphenylphosphonium chloride and 2.0 L of tetrahydrofuran (THF) were placed in a flask. During stirring at room temperature, 73.6 g of potassium t-butoxide was added to the flask. After further stirring at room temperature for 2 hours, 1.5 L of water was added. The reaction solution was extracted with diethyl ether. An aqueous phase was removed and 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 180 g (yield: 99%) of 1-bromo-4-[1-(2-methoxyvinyl)phenyl]naphthalene was obtained.

Provenance & Evidence