Potassium Carbonate → Benzonitrile, 4-[(4-fluorophenyl)methoxy]-

HRID 73146Notes

Reaction equation

HRID 73146 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

5

Reactant 3

HCID 11430Potassium CarbonateHCID 130194-CyanophenolHCID 680214-Fluorobenzyl bromide

Product 1

HCID 2243494Benzonitrile, 4-[(4-fluorophenyl)methoxy]-Yield 81.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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.

Workup

  1. temperatureat reflux (5 h)
  2. customThe volatiles were evaporated
  3. additionthe residue was diluted in CH2Cl2 (300 mL)
  4. washwashed with H2O (500 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe solid was recrystallized with MeOH

Sources & evidence

ORD record
ord-a7fb32e32b4e44e29a7e60511ee3df94
Source dataset
uspto-grants-2014_09
Patent number
US08829033B2

Reaction notes

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