Indole → 1-(3-Bromopropyl)indole

Participants

Reaction Steps

To sodium hydride (0.9 g, 30 mmol, 80% oil dispersion) and indole (2.81 g, 24 mmoles) was added anhydrous dimethylformamide (50 mL). The resultant mixture was stirred at room temperature under argon for 1 h. Then neat 1,3-dibromopropane (7.3 mL, 72 mmol) was added and the reaction mixture was stirred at room temperature for 20 h. The reaction mixture was poured into water (120 mL) and the resultant slurry was extracted with diethyl ether (3×100 mL). After the organic extracts were combined and concentrated in vacuo, the crude material was purified by dry column chromatography (350 mL funnel filled with Silica 10–40μ, Sigma cat. S-6628) using as eluent a mixture of ethyl acetate and hexanes (1:49 v/v, containing 0.2% v/v isopropylamine) to yield 1.43 g of N-(3-bromopropyl)indole.

Provenance & Evidence