4-(Bromomethyl)benzonitrile → HCID 14774146、化合物

反応式

O.O.O.O.O.[N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:7]=1[CH2:16][O:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[O-:21].[Na+].[C:26]([C:28]1[CH:35]=[CH:34][C:31]([CH2:32]Br)=[CH:30][CH:29]=1)#[N:27].O.CCOCC>CN(C=O)C>[N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:7]=1[CH2:16][O:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[O:21][CH2:32][C:31]1[CH:34]=[CH:35][C:28]([C:26]#[N:27])=[CH:29][CH:30]=1

参加物

実験手順

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 Na2SO4 /MgSO4, filtered and concentrated. The crude product is recrystallized from 70% EtOAc/hexane to obtain 4-(3-(2-quinolinylmethyloxy)phenoxymethyl)benzonitrile. (M.P. 112.5° C.)