Bromoacetonitrile → 2-((1H-Indol-4-yl)oxy)acetonitrile

HRID 8119

Reaktionsgleichung

Reaktionsgleichung von HRID 8119
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[H-].[Na+].Br[CH2:14][C:15]#[N:16]>CN(C)C=O.C(OCC)(=O)C>[NH:6]1[C:7]2[C:3](=[C:2]([O:1][CH2:14][C:15]#[N:16])[CH:10]=[CH:9][CH:8]=2)[CH:4]=[CH:5]1

Komponenten

6

Edukt 3

HCID 11534BromoacetonitrileHCID 24758Sodium hydrideHCID 754211H-indol-4-ol

Produkt 1

HCID 155417992-((1H-Indol-4-yl)oxy)acetonitrileAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A 0° C. solution of 4-hydroxyindole (20 g, 150 mmol) in 500 ml of dimethylformamide is treated with NaH (60% dispersion in mineral oil; 6.6 g, 165 mmol). After 30 minutes, bromoacetonitrile (11.5 ml, 165 mmol) is added, and the resulting mixture is allowed to slowly warm to ambient temperature and stir for 3 days. The reaction mixture is diluted with ethyl acetate and washed 3 times with H2O. The organic layer is dried over Na2SO4 and concentrated in vacuo. The crude residue is purified by normal phase HPLC (SiO2; 5% step gradient of 0 to 20% ethyl acetate in hexanes) to give 25 g of (1H-indol-4-yloxy)acetonitrile (97%).

Aufarbeitung

  1. washwashed 3 times with H2O
  2. dry with materialThe organic layer is dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude residue is purified by normal phase HPLC (SiO2; 5% step gradient of 0 to 20% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-f7a1ba14ffa947f1be82f724f443f402
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087635B2

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