Reaktion #168216

Reaktionsgleichung

3-chloro-5-(4-phenoxyphenyl)isonicotinonitrile

potassium fluoride

→

3-fluoro-5-(4-phenoxyphenyl)isonicotinonitrile

Ausbeute 69.0%

Lösungsmittel

water

DMSO

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate (3×400 mL)
2. 2
   WaschenThe combined extracts were washed with brine (100 mL)
3. 3
   Trocknendried (MgSO4)
4. 4
   Einengenconcentrated
5. 5
   WaschenSilica gel chromatography, eluting with 0-15% ethyl acetate in dichloromethane-hexanes (1:2)

Vorschrift

A mixture of 3-chloro-5-(4-phenoxyphenyl)isonicotinonitrile (11.8 g, 38.5 mmol) and potassium fluoride (11.17 g, 192 mmol) in DMSO (500 mL) was heated to 120° C. for 10 days. The mixture was diluted with water (1 L) and extracted with ethyl acetate (3×400 mL). The combined extracts were washed with brine (100 mL), dried (MgSO4) and concentrated. Silica gel chromatography, eluting with 0-15% ethyl acetate in dichloromethane-hexanes (1:2), gave 3-fluoro-5-(4-phenoxyphenyl)isonicotinonitrile as tan solid (7.66 g, 69% yield). 1H NMR (500 MHz, CDCl3) δ ppm 8.67 (1H, s), 8.64 (1H, s), 7.52-7.62 (2H, m), 7.36-7.46 (2H, m), 7.20 (1H, t, J=7.42 Hz), 7.05-7.17 (4H, m); MS (ES+) m/z: 291 (M+H); LC retention time: 4.118 min (analytical HPLC Method A).

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