Reaktion #2448791

Reaktionsgleichung

1-chloro-4,6-dimethoxyisoquinoline

cesium fluoride

→

desired compound

Ausbeute 20.1%

1-fluoro-4,6-dimethoxyisoquinoline

Ausbeute 20.1%

Lösungsmittel

water

DMSO

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction vessel (Pressure tube) was sealed
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   TrocknenThe combined organic layer was dried over anhydrous Na2SO4
4. 4
   Sonstigeevaporated under reduced pressure
5. 5
   Sonstigeto get crude compound
6. 6
   SonstigeThe crude compound was purified by silica gel chromatography

Vorschrift

To a solution of 1-chloro-4,6-dimethoxyisoquinoline (1.5 g, 6.71 mmol) in DMSO (15 ml) was added cesium fluoride (4 g, 26.8 mmol) at room temperature. The reaction vessel (Pressure tube) was sealed and heated at 145° C. for 18 h. The reaction mass was diluted with water and extracted with ethyl acetate. The combined organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography to get desired compound (280 mg, 20.15%) as white solid. 1H NMR (400 MHz, CDCl3): δ ppm 7.99-7.97 (d, J=8 Hz, 1H), 7.44-7.39 (m, 2H), 7.27-7.11 (m, 1H), 4.03 (s, 3H), 3.97 (s, 3H); 19F NMR: δ ppm −79.32 (1 F); MS: MS m/z 208.0 (M++1).

Quelle