Reaktion #453492

Reaktionsgleichung

N,N-diethylaniline

3-(4-chloro-2-fluoro-6-propargyloxyphenyl)-1-methyl-6-trifluoromethyluracil

cesium fluoride

→

desired product

Ausbeute 26.9%

3-(4-chloro-6-fluoro-2-methylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil

Ausbeute 26.9%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter completion of the reaction
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   WaschenThe organic layer was washed sequentially with a 10% hydrochloric acid aqueous solution, water
4. 4
   Trocknena saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
6. 6
   SonstigeThen, the obtained residue was purified by silica gel column chromatography

Vorschrift

100 ml of N,N-diethylaniline was added to 5.2 g (14 mmol) of 3-(4-chloro-2-fluoro-6-propargyloxyphenyl)-1-methyl-6-trifluoromethyluracil and 6.4 g (42 mmol) of cesium fluoride, followed by stirring at 180 to 190° C. for 3 hours. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with a 10% hydrochloric acid aqueous solution, water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 1.4 g (yield: 26.9%) of the desired product as white powder. Melting point: 196-197° C.

Quelle