Potassium Carbonate → (5-Chloro-2-isopropyl-4-methoxy-phenoxy)-acetonitrile

HRID 38336

Reaktionsgleichung

Reaktionsgleichung von HRID 38336
[Cl:1][C:2]1[C:3]([O:12][CH3:13])=[CH:4][C:5]([CH:9]([CH3:11])[CH3:10])=[C:6]([OH:8])[CH:7]=1.C([O-])([O-])=O.[K+].[K+].I[CH2:21][C:22]#[N:23]>CN(C=O)C>[Cl:1][C:2]1[C:3]([O:12][CH3:13])=[CH:4][C:5]([CH:9]([CH3:11])[CH3:10])=[C:6]([CH:7]=1)[O:8][CH2:21][C:22]#[N:23]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 69356IodoacetonitrileHCID 595986685-Chloro-2-isopropyl-4-methoxy-phenol

Produkt 1

HCID 59598662(5-Chloro-2-isopropyl-4-methoxy-phenoxy)-acetonitrileAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a solution of 5-chloro-2-isopropyl-4-methoxy-phenol (10.36 g, 51.6 mmol) in 40 mL DMF was added K2CO3 (8.55 g, 62.0 mmol) and the mixture was heated to 65° C. After 15 minutes iodoacetonitrile (9.05 g, 54.2 mmol) was added and the mixture was heated to 80° C. for 1 hour. The mixture was cooled, poured into an ice/H2O mixture and extracted with 1:1 toluene/hexane. The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by passing through a short plug of silica to afford (5-chloro-2-isopropyl-4-methoxy-phenoxy)-acetonitrile (11.97 g, 97%) as a white solid.

Aufarbeitung

  1. temperaturethe mixture was heated to 80° C. for 1 hour
  2. temperatureThe mixture was cooled
  3. extractionextracted with 1:1 toluene/hexane
  4. washThe combined organics were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified

Quellen und Nachweise

ORD-Eintrag
ord-8b70b4f1efbc458fbfbd3492f9d230dc
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524725B2

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