tert-Butanol → 3,3,5-Tribromo-1H-pyrrolo[2,3-b]pyridin-2(3H)-one

Participants

Reaction Conditions

Reaction Steps

Bromine (13.4 mL, 0.262 mol) was added dropwise over a period of 30 min to a cooled (ice bath) and stirred suspension of 2 (37.86 g, 0.131 mol) in water:t-BuOH=1:1 (1500 mL). Cooling bath was removed and the mixture was stirred at r.t. overnight. Then the solution was cooled to 15° C. and saturated aqueous solution of NaHCO3 (278 mL) was added. A yellow suspension, which was formed, was concentrated in vacuum (bath temperature<32° C.) until about 1000 mL of condensate was collected. The solid was filtered off, washed with water (200 mL), and dried in vacuum to afford 3 (40.85 g, 85%) as tan powder.

Provenance & Evidence