Sodium Cyanide → 6-Fluoropyridine-2-carbonitrile
Reaktionsgleichung
F[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[N:3]=1.[C-:9]#[N:10].[Na+]>CS(C)=O.CCOC(C)=O>[C:9]([C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[N:3]=1)#[N:10]Komponenten
5
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
Dissolve 2,6-difluoropyridine (12 g, 104.2 mmol) in anhydrous DMSO (5 mL). Add a solution of sodium cyanide (1.3 g, 26.53 mmol) in DMSO (60 mL) over 12 h using a syringe pump. Heat the mixture to 100° C. overnight. Cool to ambient temperature, dilute with EtOAc (500 mL), and wash with brine. Dry the organic phase over Na2SO4, filter, and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 4:1) to give the desired intermediate as a solid (723 mg, 22%). GC-MS m/z: 122 (M+).
Aufarbeitung
- temperatureCool to ambient temperature
- washwash with brine
- dry with materialDry the organic phase over Na2SO4
- filtrationfilter
- concentrationconcentrate in vacuo
- customPurify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 4:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-9218186c655044f6ab8129494ddaa55b
- Quelldatensatz
- uspto-grants-2013_11
- Patentnummer
- US08580780B2
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