Hydrochloric Acid → 2-{[1-Bromo-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetonitrile

Participants

Reaction Steps

To an ice-cooled solution of 1-[2-(5-bromo-6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-1-pentanone (1.2 g, 2.8 mmol) in dry DMF (12 mL) was added sodium hydride (0.315 g, 7.88 mmol of a 60% dispersion on mineral oil) in three portions. Bromoacetonitrile (0.49 mL, 7.0 mmol) was added and the mixture was stirred at room temperature for 1.5 hours, then poured into excess water and acidified with 2N hydrochloric acid. The mixture was extracted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography (Biotage apparatus) using 15% tert-butyl methyl ether in hexane as an eluant to afford 2-{[1-bromo-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetonitrile as a yellow solid (0.776 g, 60%), mp 98-100° C.

Provenance & Evidence