5-Cyano-2-fluorobenzaldehyde → 4-Fluoro-3-(1-hydroxyethyl)benzonitrile

HRID 398357Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 398357
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([F:11])=[C:7]([CH:10]=1)[CH:8]=[O:9])#[N:2].[CH3:12][Li]>C1COCC1>[F:11][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:10][C:7]=1[CH:8]([OH:9])[CH3:12]

Komponenten

4

Edukt 2

HCID 109097255-Cyano-2-fluorobenzaldehydeHCID 178418348HCID 178418348, Verbindung

Produkt 1

HCID 230001664-Fluoro-3-(1-hydroxyethyl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 5-cyano-2-fluorobenzaldehyde (1.50 g, 10.06 mmol) in THF (15 mL) cooled to 0° C. was added methyllithium (7.90 mL, 11.06 mmol). The mixture was stirred at room temperature for 2 h and quenched by the addition of saturated NH4Cl (10 mL). The mixture was partitioned between ethyl acetate (50 mL) and water (20 mL), the organic was washed with water (20 mL), dried over magnesium sulfate and concentrated in vacuo to provide a residue. Purification via flash column chromatography (30×150 mm column; elution with EtOAc: Hex, 1:2) afforded pure compound:

Aufarbeitung

  1. customquenched by the addition of saturated NH4Cl (10 mL)
  2. customThe mixture was partitioned between ethyl acetate (50 mL) and water (20 mL)
  3. washthe organic was washed with water (20 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto provide a residue
  7. customPurification
  8. washvia flash column chromatography (30×150 mm column; elution with EtOAc: Hex, 1:2)
  9. customafforded pure compound

Quellen und Nachweise

ORD-Eintrag
ord-78c9206df81240b7876af20d7576b8a9
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06610692B1

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