6-Bromo-3-pyridinecarboxaldehyde → 5-Formylpyridine-2-carbonitrile
Reaktionsgleichung
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][N:3]=1.[C:10]([Cu])#[N:11]>CN(C=O)C.CCOC(C)=O>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([C:10]#[N:11])=[N:3][CH:4]=1)=[O:7]Komponenten
5
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 120 °C
Versuchsvorschrift
A mixture of 6-bromonicotinaldehyde (11.2 g, 60 mmol) and CuCN (8.06 g, 90 mmol) in DMF (100 mL) was heated at 120° C. for 3 h under N2. The mixture was cooled to rt and diluted with EtOAc and filtered through a pad of celite. The organic layer was washed with water and brine and then dried (MgSO4) and concentrated. The product 5-formylpicolinonitrile (4.55 g) was obtained by silica gel chromatography (elution with 0-20% EtOAc/Hex).
Aufarbeitung
- temperatureThe mixture was cooled to rt
- filtrationfiltered through a pad of celite
- washThe organic layer was washed with water and brine
- dry with materialdried (MgSO4)
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-8e279503f927475086449129fc2db2d2
- Quelldatensatz
- uspto-grants-2015_05
- Patentnummer
- US09029362B2
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