Indole → 1-(2-chloroethyl)-1H-indole

Participants

Reaction Steps

Into a flask of 500 ml capacity fitted with a stirrer and cooling tube, there were introduced 7.2 g (corresponding to 0.21 mol) of an oil dispersion of NaH and 50 ml of tetrahydrofuran, and the mixture was stirred on an ice-water bath. Into this mixture there was added dropwise, little by little, a solution in which 24.60 g (0.21 mol) of indole were dissolved in 100 ml of tetrahydrofuran. After completion of the dropwise addition, the ice-water bath was removed and the mixture was stirred for one hour at room temperature. Then, 49.29 g (0.21 mol) of 2-chloroethyl-p-toluene sulfonate were added, and the reaction performed under heated reflux whilst stirring for 15 hours. After completion of the reaction, the undissolved material was removed by filtration, and concentration was performed under reduced pressure. This reaction mixture was purified by column chromatography using silica gel, to obtain 15.4 g of 1-(2-chloroethyl)indole.

Provenance & Evidence