1,2-Dichloroethane → 1-(5-Iodo-1H-indol-1-yl)ethanone

Participants

Reaction Steps

A solution of 5-iodo-1H-indole (530 mg, 2.18 mmol), DMAP (53 mg, 0.43 mmol), triethylamine (0.46 mL, 3.30 mmol), acetic anhydride (0.81 mL, 8.57 mmol), and 1,2-dichloroethane (5.5 mL) was heated at 60° C. overnight. The reaction mixture was diluted with ethyl acetate (100 mL), washed (50 mL saturated NH4Cl then 50 mL brine), dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography to yield the title compound as a white solid (600 mg, 96%). 1H NMR (300 MHz, DMSO-d6): δ 8.17 (d, 1H), 8.01 (d, 1H), 7.87 (d, 1H), 7.58 (dd, 1H), 6.70 (d, 1H), 2.64 (s, 3H).

Provenance & Evidence