Diethyl Ether → 2-(5-Bromo-1H-indol-1-yl)ethanol

Participants

Reaction Steps

DIBAL-H (1 M in hexanes) (6.1 mL, 6.1 mmol) was added to a 0° C. solution of methyl (5-bromo-1H-indol-1-yl)acetate (660 mg, 2.46 mmol) in anhydrous THF (12 mL). The reaction was warmed to ambient temperature and maintained for 1 h. The reaction mixture was poured into saturated aqueous Rochelle's salt (25 mL) and Et2O (25 mL). The mixture was stirred vigorously for 30 min. The layers were separated and the aqueous phase was extracted with Et2O. The combined organic layers were washed with brine, dried (Na2SO4), filtered, and concentrated to afford the desired product as a yellow oil.

Provenance & Evidence