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

Participants

Reaction Steps

The mixture of 1-[2-(5-bromo-6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-1-pentanone (1.46 g, 3.45 mmol) and cesium carbonate (2.36 g, 7.23 mmol) in acetone (16 mL) was stirred at room temperature for 15 minutes. Bromoacetonitrile (0.50 mL, 7.2 mmol) was then added and the mixture was stirred for 4 hours at room temperature then poured into excess water and extracted with ethyl acetate. The organic phase was washed with brine, dried over anhydrous magnesium sulfate, filtered and solvent evaporated. The residue was purified by flash chromatography (Biotage apparatus) using 5-20% 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 (0.989 g), mp 100-102° C. Mass spectrum (−ESI, [M−H]−) m/z 460. 1HNMR (400 MHz, DMSO-d6): δ8.55 (d, 1H, J=0.98 Hz), 8.25 (d, 2H, J=9.3 Hz), 8.0-8.05 (m, 2H), 7.7-7.75 (m, 2H), 7.4-7.5 (m, 2H), 5.5 (s, 2H), 2.75 (t, 2H, J=7.2 Hz), 1.5-1.6 (m, 2H), 1.1-1.2 (m, 2H), and 0.7 ppm (t, 3H, J=7.2 Hz). Elemental Analysis for C25H20BrNO3: Calculated: C, 64.95; H, 4.36; N, 3.03. Found: C, 64.71; H, 4.32; N, 2.86.

Provenance & Evidence