4-Methoxyphenol → 4-(4-methoxyphenoxy)benzonitrile

HRID 1909626Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1909626
I[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.C(OCC)(=O)C.Cl.CN(C)CC(O)=O>[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)=[CH:14][CH:13]=1

Komponenten

8

Edukt 3

HCID 90154-MethoxyphenolHCID 10796Cesium carbonateHCID 764674-Iodobenzonitrile

Produkt 1

HCID 14902794-(4-methoxyphenoxy)benzonitrileAusbeute 113,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 75605N,N-Dimethylglycine hydrochlorideKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 4-iodobenzonitrile (0.458 g, 2 mmol), 4-methoxyphenol (0.372 g, 3 mmol) and cesium carbonate (1.30 g, 4 mmol) in dioxane (4 mL) was added N,N-dimethylglycine hydrochloride (0.025 g, 0.18 mmol). The vessel was purged with nitrogen before Cu(I) iodide (0.014 g, 0.07 mmol) was added. The reaction mixture was heated to 90° C. overnight. The reaction mixture was diluted with water and ethyl acetate. The organic portion was washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo to give the title compound (0.51 g, 100%); 1H NMR (400 MHz, CDCl3); δ 3.83 (s, 3H), 6.92-7.02 (m, 6H), 7.56-7.58 (m, 2H).

Aufarbeitung

  1. additionwas added
  2. washThe organic portion was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-55a057baa211464e87f18419bf140c3f
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598359B2

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