Methanol → 2-(4-Bromonaphthalen-2-ylmethyl)-5-ethylbenzo[b]thiophene

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Reaction Steps

In a nitrogen stream, triethylsilane (0.63 ml, 3.93 mmol) and a boron trifluoride-diethyl ether complex (0.27 ml, 2.16 mmol) were added to a solution of (4-bromo-naphthalen-2-yl)-(5-ethylbenzo[b]-thiophen-2-yl)methanol (780 mg, 1.96 mmol) in methylene chloride (20 ml) at 0° C. and the reaction mixture was stirred at room temperature for three hours. To the obtained solution was added methanol (10 ml) and water (30 ml) 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=n-hexane)] to obtain the title compound (460 mg, 62%).

Provenance & Evidence