1,4-Dibromonaphthalene → 4-Bromo-1-naphthonitrile

HRID 45776

Reaktionsgleichung

Reaktionsgleichung von HRID 45776
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([Br:12])=[CH:4][CH:3]=1.[Cu](C#N)[C:14]#[N:15]>CN(C=O)C>[Br:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([C:14]#[N:15])=[CH:3][CH:4]=1

Komponenten

4

Edukt 2

HCID 665211,4-DibromonaphthaleneHCID 178418260HCID 178418260, Verbindung

Produkt 1

HCID 146621114-Bromo-1-naphthonitrileAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

A mixture of 1,4-dibromonaphthalene (24.06 g, 84 mmol) and copper cyanide (6.02 g, 67 mmol) in DMF (85 mL) was heated to 125° C. overnight. The mixture was partially concentrated to remove DMF and the resulting residue washed with aqueous ammonium hydroxide and extracted with ethyl acetate. The organic layer was concentrated and purified by chromatography to yield 4-bromo-1-naphthonitrile (5.13 g, 26%).

Aufarbeitung

  1. concentrationThe mixture was partially concentrated
  2. customto remove DMF
  3. washthe resulting residue washed with aqueous ammonium hydroxide
  4. extractionextracted with ethyl acetate
  5. concentrationThe organic layer was concentrated
  6. custompurified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f59ca2945eba4b08beec8ffdabe7efe7
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541589B2

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