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

HRID 749935Notes

Reaction equation

HRID 749935 reaction equation
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

Participants

8

Reactant 3

HCID 71014-BromobiphenylHCID 90154-MethoxyphenolHCID 10796Cesium carbonate

Product 1

HCID 2668644-(4-Methoxyphenoxy)biphenylYield 128.3%

Reagents, catalysts & solvents 4

HCID 75605N,N-Dimethylglycine hydrochlorideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-5a55b5283e64482b93abba784c1ebb24
Source dataset
uspto-grants-2008_07
Patent number
US07402684B2

Reaction notes

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