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

HRID 73127

Reaktionsgleichung

Reaktionsgleichung von HRID 73127
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

Komponenten

6

Edukt 4

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

Produkt 1

HCID 22293834-[(3-Fluorophenyl)methoxy]benzonitrileAusbeute 87,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

(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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8541a7b1c057457fbe210b8acc3919ea
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829033B2

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