Dimethylformamide → 5-Bromo-3-methylpyridine-2-carbonitrile

HRID 339980

Reaktionsgleichung

Reaktionsgleichung von HRID 339980
Br[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.[CH3:10][N:11](C)C=O.[Cu](C#N)C#N>>[Br:9][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([C:10]#[N:11])=[N:3][CH:4]=1

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 8176802,5-Dibromo-3-methylpyridineHCID 178418260HCID 178418260, Verbindung

Produkt 1

HCID 207750075-Bromo-3-methylpyridine-2-carbonitrileAusbeute 49,4 %

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of 2,5-dibromo-3-methylpyridine (5.0 g, 20. mmol) in N,N-dimethylformamide (20.0 mL, 259 mmol) was added copper cyanide (1.8 g, 20. mmol) and the reaction was stirred at 120° C. for 12 h. The reaction was partitioned between EtOAc and water. The organic layer was washed with brine, dried over sodium sulfate, filtered, concentrated and purified by combi-flash chromatography to afford 1.94 g (49% yield) of the desired product as a white solid.

Aufarbeitung

  1. customThe reaction was partitioned between EtOAc and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by combi-flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-52a681ab55184b49a6001931513cf1c5
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895571B2

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