Indole → 1H-Indole-1-acetic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 2-bromoacetate (25 g, 0.15 mole) and indole (11.7 g, 0.1 mole) in 100 ml of benzene is added a solution of sodium hydroxide (25 g, 0.626 mole) in 50 ml of water. To the obtained mixture is added tetra-n-butylammonium bromide (1.6 g, 0.5 mmole). The mixture is stirred at 25° C. for 16 hours. The aqueous phase is acidified to pH 3. The organic phase is separated, dried and evaporated to give the title compound in 92% yield. NMR (DMSO-D6) ppm (δ) 5.05 (s, 2); 6.50 (d, 1), 6.9-7.8 (m, 5).

Provenance & Evidence