Phenylacetyl chloride → HCID 21075900, compound

Participants

Reaction Steps

To a 0° C. mixture of (6-benzo[b]thiophen-2-yl-1-bromo-naphthalen-2-yloxy)-acetonitrile (4.87 g, 12.4 mmol) in chloroform (250 mL) was added phenylacetyl chloride (2.0 mL, 15 mmol) and tin (IV) chloride (2.2 mL, 19 mmol). It was refluxed for five hours. During reflux, additional phenylacetyl chloride (2.0 mL, 15 mmol) and tin (IV) chloride (2.2 mL, 19 mmol) were added. The reaction mixture was then allowed to cool to ambient temperature and poured into ice water. It was diluted with additional chloroform and washed with water and brine. It was then dried with anhydrous magnesium sulfate, filtrered and solvent evaporated. After stirring the residue in ether and filtering, the filtrate was concentrated and purified by flash chromatography using 25–45% methylene chloride in hexane and 100% methylene chloride as eluent and then further purified by HPLC using 86% acetonitrile (0.1% formic acid) as the mobile phase. Evaporating the solvent and extracting with ethyl acetate, washing with water and brine, drying with anhydrous magnesium sulfate, filtering, concentrating and drying in vacuo at 60° C. for one hour yielded the title compound as a hard amber gum (0.531 g, 8.36%); mass spectrum (+EI, [M+H]+) m/z 512/514. 1H NMR (500 MHz, DMSO-d6): δ8.30 (d, 1H, J=8.70 Hz), 7.74 (d, 1H, J=9.17 Hz), 7.85 (dd, 1H, J=8.70 Hz and 1.83 Hz), 8.21–8.25 (m,2H), 8.07–8.10 (m, 1H), 7.90–7.94 (m, 1H), 7.44–7.50 (m, 2H), 7.13–7.19 (m, 3H), 6.91–6.94 (m, 2H), 5.47 (s, 2H), 3.8 ppm (s, 2H). Elemental Analysis for C28H18BrO2S: Calcd: C, 65.63; H, 3.54; N, 2.73; Found: C, 65.48; H, 3.43; N, 2.35.

Provenance & Evidence