Indole → 1-(3-Bromopropyl)indole

Participants

Reaction Conditions

Reaction Steps

9.58 g of potassium hydroxide (KOH) and 20.00 g of indole were added to 110.58 g of 1,3-dibromopropane and 450 mL of N,N-dimethylformamide (DMF), and the mixture was stirred at 70° C. for 8 hours. After cooling to room temperature, 1 L of distilled water was added to the reaction solution, and the resulting solution was extracted with 1 L of ethyl acetate. The organic layer was washed with 500 mL of distilled water five times, then concentrated and purified by column chromatography to obtain 27.24 g of N-(3-bromopropyl)-indole. Compounds (p-9) and (p-10) having a bromopropyl group shown below were also synthesized in the same manner.

Provenance & Evidence