Potassium Carbonate → 4-[(4-Fluorophenyl)methoxy]benzonitrile

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].C([O-])([O-])=O.[K+].[K+].[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Br)=[CH:19][CH:18]=1>CC(C)=O>[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][O:9][C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)=[CH:19][CH:18]=1

Participants

Procedure

A mixture of 4-cyanophenol (11.91 g, 100.0 mmol), K2CO3 (55.20 g, 400.0 mmol), and 4-fluorobenzylbromide (22.68 g, 120.0 mmol) were heated in acetone (400 mL) at reflux (5 h). The volatiles were evaporated and the residue was diluted in CH2Cl2 (300 mL), and then washed with H2O (500 mL), dried (MgSO4), and concentrated in vacuo. The solid was recrystallized with MeOH to give white needles (18.50 g, 81%): Rf=0.89 (hexanes/EtOAc 911); mp 82-83° C.; 1H NMR (CDCl3) δ 5.07 (s, CH2O), 7.01 (d, J=9.0 Hz, 2 ArH), 7.09 (t, J=8.7 Hz, 2 ArH), 7.37-7.42 (m, 2 ArH), 7.59 (d, J=9.0 Hz, 2 ArH); 13C NMR (CDCl3) δ 69.5 (CH2O), 104.2 (CCN), 115.5 (ArC), 115.6 (d, J=22.5 Hz, C3′), 119.0 (CN), 129.4 (d, J=7.9 Hz, C2′), 131.4 (C1′), 133.9 (ArC), 161.7 (ArC), 162.6 (d, J=245.6 Hz, C4′); Anal. Calcd. for C14H10FNO2: C, 74.00; H, 4.44; F, 8.36; N, 6.16. Found: C, 74.06; H, 4.28; F, 8.26; N, 6.16.