4-Bromobiphenyl → 4-(4-Methoxyphenoxy)biphenyl

HRID 749935Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 749935
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.C(OCC)(=O)C.Cl.CN(C)CC(O)=O>[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:4][CH:3]=2)=[CH:18][CH:17]=1

Komponenten

8

Edukt 3

HCID 71014-BromobiphenylHCID 90154-MethoxyphenolHCID 10796Cesium carbonate

Produkt 1

HCID 2668644-(4-Methoxyphenoxy)biphenylAusbeute 128,3 %

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-bromobiphenyl (1.00 g, 4.29 mmol), 4-methoxyphenol (0.35 g, 2.82 mmol) and cesium carbonate (1.85 g, 5.68 mmol) in dioxane (10 mL) was added N,N-dimethylglycine hydrochloride (0.04 g, 0.26 mmol). The vessel was purged with nitrogen before Cu(I) iodide (0.02 g, 0.11 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 (1.00 g, 100%) as a light green solid.

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-5a55b5283e64482b93abba784c1ebb24
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07402684B2

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