N-bromobutanimide → HCID 10623988, compound

Participants

Reaction Steps

2-Bromo-5-methoxy-!-(phenylmethyl)-1H-indole-3-acetic acid benzyl ester. N-Bromosuccinimide (450 mg, 2.5 mmol) was added to 910 mg (2.5 mmol) of 5-methoxy-1-phenylmethyl)-1H-indole-3-acetic acid benzyl ester in 75 mL of carbon tetrachloride and the mixture stirred for 0.5 hour. After washing with Na2S2O3 solution, water and saturated NaCl solution and drying (Na2SO4), the CCl4 was removed at reduced pressure. The residue was chromatographed on silica (eluted with methylene chloride) and crystallized from ether/hexane to give 765 mg (67% yield) of 2-bromo-5-methoxy-1-(phenylmethyl)-1H-indole-3-acetic acid benzyl ester, mp, 89-90° C.

Provenance & Evidence