N-bromobutanimide → Tert-butyl 2-bromo-4,5,7,8-tetrahydrofuro[3,2-c]azepine-6-carboxylate

Participants

Reaction Steps

A solution of tert-butyl 4,5,7,8-tetrahydrofuro[3,2-c]azepine-6-carboxylate (0.21 mmol) in chloroform (0.5 mL) and acetic acid (0.5 mL) is treated with N-bromosuccinimide (0.21 mmol) at RT. After 1 hour, the reaction is poured over saturated aqueous NaHCO3, and extracted with ethyl acetate (2×5 mL). The organic layers are washed with brine, dried, and purified by silica chromatography (20% ethyl acetate/hexanes) to give tert-butyl 2-bromo-4,5,7,8-tetrahydrofuro[3,2-c]azepine-6-carboxylate.

Provenance & Evidence