Benzyl Alcohol → 4-Benzyloxy-3,5-difluorobenzonitrile

HRID 2236371Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2236371
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:11])[C:9]=1F)[C:5]#[N:6].[CH2:12]([OH:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[H-].[Na+].Cl>CN(C=O)C>[CH2:12]([O:19][C:9]1[C:8]([F:11])=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[F:1])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

6

Edukt 4

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 5938143,4,5-Trifluorobenzonitrile

Produkt 1

HCID 574457224-Benzyloxy-3,5-difluorobenzonitrileAusbeute 89,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 5.0 g of 3,4,5-trifluorobenzonitrile and 4.5 g of benzyl alcohol in 25 ml of DMF was added 1.5 g of 60% sodium hydride (oily) at 0° C. The mixture was stirred at room temperature for 4 hours. Then, dilute hydrochloric acid was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 7.0 g of 4-benzyloxy-3,5-difluorobenzonitrile represented by the formula:

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2bcb7f931c734b518f99d895c16d61c1
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07714168B2

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