Chloroacetonitrile → 3-Fluorophenoxyacetonitrile

HRID 18800

Reaktionsgleichung

Reaktionsgleichung von HRID 18800
[F:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:16][C:17]#[N:18]>CN(C=O)C.CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:16][C:17]#[N:18]

Komponenten

6

Edukt 3

HCID 7856ChloroacetonitrileHCID 97433-FluorophenolHCID 11430Potassium Carbonate

Produkt 1

HCID 150774063-FluorophenoxyacetonitrileAusbeute 94,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 3-fluorophenol (560 mg, 5.0 mmol) in DMF (10 mL) is added potassium carbonate (828 mg, 6.0 mmol) followed by chloroacetonitrile (0.315 mL, 50.0 mmol). The reaction mixture is stirred and heated at 50° C. for 14 h. The reaction mixture is cooled to RT, diluted with EtOAc, and washed with water, brine, then dried (MgSO4), and filtered. The filtrate is evaporated, and the residue purified by chromatography on silica gel; elution with dichloromethane gives 712 mg of the product 386.

Aufarbeitung

  1. temperatureThe reaction mixture is cooled to RT
  2. washwashed with water, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customThe filtrate is evaporated
  6. customthe residue purified by chromatography on silica gel
  7. washelution with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-679042b22ecb452c904ab20fb5acda8e
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741493B2

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