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

HRID 1909626Notes

Reaction equation

HRID 1909626 reaction equation
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

Participants

8

Reactant 3

HCID 90154-MethoxyphenolHCID 10796Cesium carbonateHCID 764674-Iodobenzonitrile

Product 1

HCID 14902794-(4-methoxyphenoxy)benzonitrileYield 113.2%

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-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).

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-55a057baa211464e87f18419bf140c3f
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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