Potassium Carbonate → HCID 18671676, compound

Participants

Reaction Steps

A mixture of 9-benzyl-8-fluoro-9H-carbazol-4-ol (1.0775 g, 0.0037 mol), potassium carbonate (0.6284 g, 0.0046 mol), bromoacetonitrile (0.6 mL, 0.0086 mol) and DMF (12 mL) is stirred at room temperature for 4 h. The mixture is then partitioned between water and dichloromethane. The aqueous layer is also washed with ethyl acetate. The combined organic layers are dried over sodium sulfate and concentrated to a residue, which is then partitioned between water and ethyl acetate. The combined organic layers are dried over magnesium sulfate and concentrated to a residue. The resulting residue is chromatographed on silica gel (100 mL) using ethyl acetate/hexane (20/80) followed by dichloromethane (100 %). The solids are recrystallized from ethyl acetate/heptane to give 0.8869 g (73%) of the title compound; mp 134-134.25° C.; MS (ESI+) for C21H15FN2O m/z 353.1 (M+Na)+; IR(drift) 1578, 1500, 1458, 1439, 1369, 1344, 1335, 1323, 1278, 1235, 1144, 1080, 793, 739, 695 cm−1; 1H NMR (CDCl3) δ5.05, 5.71, 6.75, 7.16, 7.24, 7.41, 8.07. Anal. Calcd for C21H15FN2O: C, 76.35; H, 4.58; N, 8.48. Found: C, 76.15; H, 4.63; N, 8.35.

Provenance & Evidence