4-Bromo-2-fluorophenol → 3-Fluoro-4-hydroxybenzonitrile

HRID 263493

Reaktionsgleichung

Reaktionsgleichung von HRID 263493
Br[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[CH:3]=1.[C:10]([Cu])#[N:11]>CN1C(=O)CCC1.CCOCC>[C:10]([C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[CH:3]=1)#[N:11]

Komponenten

5

Edukt 2

HCID 27249814-Bromo-2-fluorophenolHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 27829443-Fluoro-4-hydroxybenzonitrileAusbeute 96,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

4-Bromo-2-fluorophenol (10 ml, 91 mmol) and 9.85 g (0.11 mol) of CuCN were combined in 75 ml of NMP with stirring under nitrogen, and the mixture was heated at 150° C. for 5 h. The mixture was diluted with 200 ml of ether, stirred, and decanted. The residue was diluted again with 200 ml of ether, heated, and decanted. The combined decantates were washed with water, 1N HCl solution, water, and brine, and dried over magnesium sulfate. The organic solution was concentrated in vacuo to provide 12 g of a white solid which was triturated in carbon tetrachloride and filtered to afford 7.29 g (72.1%) of the title compound.

Aufarbeitung

  1. stirringstirred
  2. customdecanted
  3. additionThe residue was diluted again with 200 ml of ether
  4. temperatureheated
  5. customdecanted
  6. washThe combined decantates were washed with water, 1N HCl solution, water, and brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationThe organic solution was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a9f37634b6b8400d9b8a6ba72ce3732a
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05643929

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