Chlorosuccinimide → 3-Chloro-1H-indole-5-carboxylic acid methyl ester

Participants

Reaction Steps

A solution of methyl 5-indolecarboxylate (501.1 mg, 2.65 mmol) in methanol (15 mL) was treated with N-chlorosuccinimide (425.4 mg, 3.18 mmol), stirred for 18 hours, and concentrated. The concentrate was dissolved into ethyl acetate, and this solution was washed with 1M NaHCO3 (2×), dried (MgSO4), filtered, and concentrated. The concentrate was purified on silica gel with 15% ethyl acetate/hexanes to provide 368.8 mg of the desired product.

Provenance & Evidence