4-(Bromomethyl)benzonitrile → HCID 18989291, compound

Participants

Reaction Steps

22.0 g (144.5 mmol) of N-isocyanoacetylpiperidine in 160 ml of THF were added dropwise to 159 mmol of lithium diisopropylamide in 430 ml of THF at -70° C. Subsequently 28.3 g (144.5 mmol) of p-cyanobenzyl bromide dissolved in 300 ml of THF were added dropwise to the mixture at -70° C. and, after stirring at this temperature for 3 h (reaction complete according to TLC, mobile phase CH2Cl2 /CH3OH 9/1), 70 ml of water were added dropwise. The solution was concentrated under reduced pressure, the residue was acidified with 1N HCl and extracted with methylene chloride, and the organic phase was dried over magnesium sulfate and evaporated. The solid product was mixed with ether, stirred overnight and filtered off with suction. 30.9 g (plus 3.3 g by working up the mother liquor) of 3-(p-cyanophenyl)-2-isocyanopropionylpiperidine were obtained as a white solid (86% of theory).

Provenance & Evidence