4-(Bromomethyl)benzonitrile → HCID 14774146, compound

Participants

Reaction Steps

A solution of 7.24 g (19.92 mmol) of sodium 3-(2-quinolinylmethyloxy)phenoxide pentahydrate and 4.68 g (23.90 mmol) of p-cyanobenzyl bromide in 34 ml of dry DMF is stirred at 75° C. under nitrogen for 2 days. The reaction mixture is cooled to room temperature, then poured into 400 ml of 3:1 H2O/Et2O, shaken, and the phases separated. The aqueous layer is extracted and washed with 1:1 brine/H2O and brine. The ether solution is dried over 1:1 Na2SO4MgSO4, filtered and concentrated. The crude product is recrystallized from 70% EtOAc/hexane to obtain 4-(3-(2-quinolinylmethyloxy)phenoxy-methyl)benzonitrile. (M.P. 112.5° C.)

Provenance & Evidence