Hydrochloric Acid → 4-(4-Methoxyphenoxy)biphenyl

HRID 749994

Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

To a solution of 4-methoxyphenol (3.99 g, 32.17 mmol) and 4-bromobiphenyl (5 g, 21.45 mmol) in anhydrous dioxane (40 mL) were added cesium carbonate (13.98 g, 42.9 mmol) and N,N-dimethylglycine.HCl (0.898 g, 6.4 mmol). The reaction mixture was flushed with nitrogen. Copper (I) iodide (0.408 g, 2.145 mmol) was added and the reaction mixture was stirred at 90° C. for 18 h under an atmosphere of nitrogen. The mixture was diluted with water (100 mL) and extracted with EtOAc (250 mL). Aqueous layer was re-extracted with EtOAc (150 mls). The organic layers were combined, dried over anhydrous Na2SO4, and concentrated to obtain the title product 7.84 g.

Aufarbeitung

customThe reaction mixture was flushed with nitrogen
extractionextracted with EtOAc (250 mL)
extractionAqueous layer was re-extracted with EtOAc (150 mls)
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-911a70802ff449069dc709acb0634781
Quelldatensatz: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07402684B2

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