Sodium Hydroxide → HCID 22310831, compound

Participants

Reaction Steps

Powdered sodium hydroxide (0.5 g) was added in a single portion to a vigorously stirred solution of ethyl 3-bromoindole-2-carboxylate (0.3 g), 3,4-dichlorobenzyl bromide (0.32 g) and tetra-n-butylammonium hydrogensulphate (50 mg) in dichloromethane. The reaction was stirred for 3 hours then partitioned between 2M HCl and ethyl acetate. Combined organic extracts were dried (MgSO4) and concentrated in vacuo and the residue purified by column chromatography using isohexane-5% ethyl acetate as eluent to give the desired end product as a colourless oil (0.35 g, 73%); NMR δ (CDCl3) 1.42 (t, 3H), 4.41 (q, 2H), 5.73 (s, 2H), 6.84 (d, 1H), 7.18-7.40 (m, 5H), 7.74 (d, 11H); M/z (+) 428 (MH+), 426, 346, 159.

Provenance & Evidence