Water → 2-Chloro-4-fluoro-3-(hydroxymethyl)benzonitrile

HRID 2046655Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2046655
[Cl:1][C:2]1[C:9]([CH:10]=[O:11])=[C:8]([F:12])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[BH4-].[Na+].O>CO>[Cl:1][C:2]1[C:9]([CH2:10][OH:11])=[C:8]([F:12])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Komponenten

5

Edukt 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 593704912-Chloro-4-fluoro-3-formylbenzonitrile

Produkt 1

HCID 593704972-Chloro-4-fluoro-3-(hydroxymethyl)benzonitrileAusbeute 67,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution (10 mL) of 2-chloro-4-fluoro-3-formylbenzonitrile (600 mg) in methanol was added sodium borohydride (136 mg) under ice-cooling, and the mixture was stirred at room temperature for 30 min. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was crystallized from hexane-isopropyl ether to give the title compound as a pale-yellow solid (yield: 410 mg).

Aufarbeitung

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was crystallized from hexane-isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-98683fbb4eb04fcabeec4259eadb7510
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592452B2

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