Benzyl Bromide → Ethyl 7-(benzyloxy)-4-formyl-1H-indole-2-carboxylate

Participants

Reaction Steps

2.33 g of 4-formyl-7-hydroxyindole-2-carboxylic acid ethyl ester is combined with 1.8 ml of benzyl bromide, 1 g of potassium carbonate, and 100 ml of acetone and heated under reflux for 4 hours. The reaction mixture is then evaporated to dryness, combined with water, and extracted with ethyl acetate. The organic phase is washed twice with saturated sodium bicarbonate solution, dried over sodium sulfate, concentrated, and recrystallized from ethyl acetate/hexane, thus obtaining 1.8 g of 7-benzyloxy-4-formylindole-2-carboxylic acid ethyl ester, mp 131°-132° C.

Provenance & Evidence