Dimethylformamide → 2-Fluoro-4-(methylsulfonyl)benzonitrile
Reaktionsgleichung
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][C:8]=1[F:17])(=O)=O.[CH3:20][N:21](C=O)C>C(OCC)(=O)C.[Cl-].[Na+].O.[C-]#N.[Zn+2].[C-]#N>[F:17][C:8]1[CH:9]=[C:10]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:11]=[CH:12][C:7]=1[C:20]#[N:21]Komponenten
6
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
To a stirred solution of the product from Step D (662 mg, 2.06 mmol) in DMF (8 mL) was added zinc cyanide (951 mg, 8.1 mmol), and the reaction was then heated at 80° C. for 12 h. The reaction mixture was diluted with ethyl acetate and poured into brine. The organic phase was separated, and the aqueous phase was extracted with two portions of ethyl acetate. The combined organic layers were washed with brine and concentrated in vacuo. Purification by flash chromatography (50:50 hexanes/ethyl acetate) afforded the desired product.
Aufarbeitung
- customThe organic phase was separated
- extractionthe aqueous phase was extracted with two portions of ethyl acetate
- washThe combined organic layers were washed with brine
- concentrationconcentrated in vacuo
- customPurification by flash chromatography (50:50 hexanes/ethyl acetate)
Quellen und Nachweise
- ORD-Eintrag
- ord-49e8a3743ee341ad87cf1910c6d02962
- Quelldatensatz
- uspto-grants-2010_03
- Patentnummer
- US07687492B2
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