Carbon tetrabromide → 3-(3-Bromopropyl)-5-nitro-1H-indole

Participants

Reaction Steps

To a solution of triphenylphosphine (6.70 g, 0.025 mol) in 80 mL of acetonitrile was added a solution of 5-nitro-3-(3-hydroxypropyl)indole (4.30 g, 0.020 mol) in 75 mL of acetonitrile, followed by a solution of CBr4 (9.00 g, 0.027 mol) in 25 mL of acetonitrile, at 0° C. under Ar. The mixture was stirred at room temperature for 3 h and then it was evaporated and the residue was chromatographed (SiO2 /EtOAc-hexane, 1:9 then 1:4) to give the title compound (4.60 g, 84%) as a solid, m.p. 92°-95° C.

Provenance & Evidence