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Water → 3,4-Difluoro-5-formylbenzonitrile

HRID 34023
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 34023
Br[C:2]1[CH:3]=[C:4]([F:11])[C:5]([F:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[Cu](C#N)[C:13]#[N:14].C(OCC)(=O)C.O>CN1CCCC1=O>[F:11][C:4]1[CH:3]=[C:2]([CH:9]=[C:6]([CH:7]=[O:8])[C:5]=1[F:10])[C:13]#[N:14]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 230701825-Bromo-2,3-difluorobenzaldehydeHCID 178418260HCID 178418260, Verbindung

Produkt 1

HCID 230702283,4-Difluoro-5-formylbenzonitrileAusbeute 42,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387
N-methyl-2-pyrrolidone
Lösungsmittel

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

To a solution of 10.0 g of 5-bromo-2,3-difluorobenzaldehyde in 40.0 mL of 1-methyl-2-pyrrolidone was added 4.26 g of copper cyanide (I) at room temperature and stirred at 170° C. for 8 hours. Adding ethyl acetate and water, the solution was stirred, and insoluble substances were filtered out through celite. The organic layer of filtrate was washed successively with saturated aqueous ammonium chloride, water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane=1:20), to afford 2.64 g of the title compound as colorless crystals.

Aufarbeitung

  1. filtrationinsoluble substances were filtered out through celite
  2. washThe organic layer of filtrate was washed successively with saturated aqueous ammonium chloride, water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe crude product was purified
  6. customseparated by silica gel column chromatography (ethyl acetate:n-hexane=1:20)

Quellen und Nachweise

ORD-Eintrag
ord-4c1e5206dc544587b892eaf2c3a9dbe2
Quelldatensatz
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07429609B2

Notizen zur Reaktion

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