Allyl bromide → Ethyl 5-[(prop-2-en-1-yl)oxy]-1H-indole-2-carboxylate

Participants

Reaction Steps

To a solution of 5-hydroxyindole-2-carboxylic acid ethyl ester (14.2 g, 68.5 mmol) in DMF (150 mL) was added cesium carbonate (26.8 g, 82.3 mmol). The resulting mixture was stirred at room temperature for 20 min followed by the addition of allyl bromide (5.94 mL, 68.5 mmol). The reaction mixture was stirred at room temperature for 24 h. The reaction was diluted with ethyl acetate, washed with H2O, brine and dried (Na2SO4). The solvent was removed in vacua and the resulting crude product was purified by flash column chromatography on silica gel (0-20% EtOAc/hexanes) to give the desired material as solid (8.9 g, 52%). LC/MS (ES+) m/e 248 [M+H]+.

Provenance & Evidence