Benzyl Bromide → HCID 67359429, compound

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of crude 8-chloro-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid (4.45 g, 17.8 mmol) and cesium carbonate (2.90 g, 8.92 mmol) in ethanol (150 ml) and water (25 ml) is refluxed until a clear solution is obtained (15 min). Then the solvents are evaporated and the dried residue is dissolved in dry DMF. This solution is treated with benzylbromide (2.27 ml, 18.7 mmol) and stirred at 45° C. for 15 min. The resulting precipitate is filtered off and the filtrate is concentrated. The residue is purified by flash chromatography on silica gel (heptane/EtOAc 3:1) to deliver pure title compound as a yellowish solid (4.2 g) in 69% yield. tR (LC-5) 1.09 min; ESI-MS (positive ion): m/z 340.19 [M+H]+ (calcd 339.82 for C20H18NO2Cl). 1H-NMR (DMSO-d6): 1.90 (m, 1H); 2.19 (m, 1H); 2.86 (m, 5H); 5.13 (s, 2H); 6.91 (t, J=7.6 Hz, 1H); 7.04 (d, J=7.6 Hz, 1H); 7.32 (m, 6H); 11.0 (br s, 1H).

Provenance & Evidence