Indole → 1-(4-Chlorobenzyl)-1h-indole

Participants

Reaction Conditions

Reaction Steps

A solution of 5.86 g (0.05 mol) of indole in 25 ml of DMSO is added to a mixture of 1.32 g of sodium hydride (0.055 mol, mineral oil suspension) in 50 ml of dimethyl sulfoxide. The resultant mixture is heated at 60° C. for 1.3 hours; after that, it is allowed to cool down and 17.7 g (0.11 mol) of 4-chlorobenzyl chloride are added dropwise. The solution is heated to 60° C. and allowed to stand overnight; it is then poured into 200 ml of water while stirring. This mixture is extracted several times with a total of 75 ml of CH2Cl2, after which the organic phase is dried with anhydrous sodium sulfate and filtered and the filtrate is evaporated in vacuo.

Provenance & Evidence