Carbon tetrabromide → HCID 69834067, compound

Participants

Reaction Steps

Triphenylphosphine (0.55 g) was added in small portions over 2 hours to a stirred solution of carbon tetrabromide (0.47 g) and methyl N-(3,4-diclilorobenzyl)-4-(hydroxyethyloxy)indole-2-carboxylate (0.28 g) in dichloromethane (10 ml). The reaction was stirred for 3 hours at room temperature, concentrated in vacuo and the residue purified by column chromatography using dichloromethane as eluent to give methyl N-(3,4-dichlorobenzyl)-4-(bromoethyloxy)indole-2-carboxylate as a white solid (0.29 g, 90%); NMR d (CD3SOCD3) 3.80 (s, 3H), 3.89 (t, 2H), 4.46 (t, 2H), 5.80 (s, 2H), 6.62 (d, 1H), 6.88 (dd, 1H), 7.17 (d, 1H), 7.25 (t, 1H), 7.30-7.36 (m, 2H), 7.52 (d, 1H), M/z (+) 456, 458 (MH+).

Provenance & Evidence