Potassium Carbonate → 4-[(3-Fluorophenyl)methoxy]benzonitrile

HRID 1425694Notes

Reaction equation

HRID 1425694 reaction equation
OC1O[C@H](C)[C@H](O)C[C@H]1O.[C:11]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)#[N:12].C([O-])([O-])=O.[K+].[K+].[F:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH2:30]Br>CC(C)=O>[F:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH2:30][O:19][C:16]1[CH:17]=[CH:18][C:13]([C:11]#[N:12])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 130194-CyanophenolHCID 680073-Fluorobenzyl bromideHCID 160540D-Abequose

Product 1

HCID 22293834-[(3-Fluorophenyl)methoxy]benzonitrileYield 87.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

(Nakamoto, Kazutaka; Tsukada, Itaru; Tanaka, Keigo; Matsukura, Masayuki; Haneda, Toru; Inoue, Satoshi; Ueda, Norihiro; Abe, Shinya; Hata, Katsura; Watanabe, Naoaki, WO 2005033079 (2005)). A mixture of 4-cyanophenol (11.91 g, 100.0 mmol), K2CO3 (55.20 g, 400.0 mmol), and 3-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 to give white needles (19.81 g, 87%): Rf=0.45 (hexanes/EtOAc 9/1); mp 104-105° C.; 1H NMR (CDCl3) δ 5.11 (s, CH2O), 6.98-7.20 (m, 5 ArH), 7.33-7.41 (m, 1 ArH), 7.59 (d, J=8.7 Hz, 2 ArH); HRMS (M+Na+)(ESI+) 250.0641 [M+Na+] (calcd for C14H10NONa+ 250.0641).

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

Sources & evidence

ORD record
ord-f498d336e90049d89ed5ea838d3a0d2f
Source dataset
uspto-grants-2015_01
Patent number
US08933065B2

Reaction notes

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