N-bromobutanimide → methyl 3-bromo-6-(methyloxy)-1H-indole-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

2-Methoxycarbonyl-6-methoxy-1H-indole (1.00 g; mfd. by Aldrich) was dissolved in DMF (51.2 mL) under an argon atmosphere, followed by stirring at 0° C. A solution of N-bromosuccinimide (1.02 g) in DMF (21.7 mL) was added dropwise over 30 minutes. The reaction mixture was maintained at 0° C. and stirred for 2.5 hours. The reaction mixture was poured into an ice water. After stirring, the resulting mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium bicarbonate solution and saturated brine, and then dried. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (4:1-3:1 hexane/ethyl acetate) to yield the title compound (760 mg).

Provenance & Evidence