Benzo(B)Thiophene → (Benzo[b]thiophen-2-yl)-(4-bromo-naphthalen-2-yl)methanol

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, an n-butyllithium hexane solution (1.6 M, 2.04 ml, 3.27 mmol) was added dropwise to a solution of benzothiophene (0.48 g, 3.58 mmol) in anhydrous THF (10 ml) at −78° C. over 5 minutes. The reaction solution was stirred at −78° C. for 10 minutes, and then at room temperature for 20 minutes. A solution of 4-bromonaphathalene-2-carbaldehyde (0.73 ml, 3.11 mmol) in anhydrous THF (5 ml) was added dropwise to the resulting reaction mixture at −78° C. and stirred at −78° C. for two hours. To the reaction mixture, a saturated ammonium chloride aqueous solution was added and the resulting mixture was extracted with diethyl ether, and the organic layer was washed with a saturated sodium chloride aqueous solution and then dried with anhydrous magnesium sulfate. After filtration, the solvent was distilled under reduced pressure and the obtained residue was purified by silica gel flash column chromatography [n-hexane:ethyl acetate (10:1)] to obtain the title compound (1.0 g, 75.6%).

Provenance & Evidence