Methanol → 2-(4-Bromonaphthalen-2-ylmethyl)-benzo[b]thiophene

Participants

Reaction Steps

In a nitrogen stream, triethylsilane (0.48 ml, 3.01 mmol) and a boron trifluoride-diethyl ether complex (0.34 ml, 2.71 mmol) were added dropwise to a solution of (benzo[b]-thiophen-2-yl)-(4-bromonaphthalen-2-yl)methanol (1.0 g, 2.71 mmol) in methylene chloride (30 mL) at 0° C. The reaction mixture was stirred at room temperature for three hours, and then a 50% methanol aqueous solution (1 ml) was added and further water was added thereto and the mixture was extracted with methylene chloride. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:40)] to obtain the title compound (0.82 g, 85.6%).

Provenance & Evidence