1-[-2-(3-Benzyloxy-6-bromo-2-nitro-phenyl)-vinyl]-pyrrolidine → 7-(Benzyloxy)-4-bromo-1H-indole

Participants

Reaction Steps

1-[-2-(3-Benzyloxy-6-bromo-2-nitro-phenyl)-vinyl]-pyrrolidine (10 g, 24.8 mmol; Intermediate 82) suspended in HOAc (25 mL) was added to a boiling mixture of iron (4.15 g, 74.4 mmol) in HOAc. After 2 h boiling TLC indicated that no starting material is left. The reaction mixture was filtered while still warm. The residue was evaporated and dissolved in toluene. The toluene slurry was applied to a silica column and eluted with toluene/hexane 1/1. Obtained 3.1 g. MS (ESI+) for C15H12BrNO m/z 302, 304 (M+H)+.

Provenance & Evidence