N-bromobutanimide → Ethyl 3-bromo-5-chloro-1H-indole-2-carboxylate

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Reaction Steps

N-Bromosuccinimide (440 mg) was added to a solution of 5-chloroindole-2-carboxylic acid ethyl ester (500 mg) in N,N-dimethylformamide (10 mL) under ice cooling. The reaction mixture was stirred at room temperature for 18 hours, and the solvent was distilled away under reduced pressure. The residue was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate, and the organic layers were combined. The combined organic layer was washed with saturated brine, and was dried over sodium sulfate anhydrate. The solvent was distilled away, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9). The thus-obtained white powder was washed with hexane, to thereby give the title compound (680 mg).

Provenance & Evidence