Water → 2-Acetylindole

Participants

Reaction Steps

A 1.0 M solution of SnCl4 (10 mL, 10.0 mmol) was added to a stirred solution of 5-bromoindole (ab) (980 mg, 5.0 mmol) and acetyl chloride (0.714 mL, 785 mg, 10.0 mmol) in 20 mL of dry toluene at 0° C. The resulting mixture was stirred at room temperature during 4 hours, and then 50 ml, of water was added. The mixture was extracted with EtOAc (3×20 mL) and the collected organic layers were washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated under vacuum. Column chromatography using EtOAc-pentane (from 5/95 to 80/20) yielded pure acetylindole (jb) (1.0 g, 4.2 mmol) as a white solid. Yield: 84%.

Provenance & Evidence