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

HRID 1909626노트

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HRID 1909626 반응식
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

참가 물질

8

반응물 3

HCID 90154-MethoxyphenolHCID 10796Cesium carbonateHCID 764674-Iodobenzonitrile

생성물 1

HCID 14902794-(4-methoxyphenoxy)benzonitrile수율 113.2%

시약·촉매·용매 4

HCID 75605N,N-Dimethylglycine hydrochloride촉매HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
90 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-55a057baa211464e87f18419bf140c3f
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598359B2

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