Reaktion #49756

Reaktionsgleichung

2-fluoro-4-chloro-5-methoxycarbonyloxyaniline

3,4,5,6-tetrahydrophthalic anhydride

water

→

N-(2-fluoro-4-chloro-5-methoxycarbonyloxyphenyl)-3,4,5,6-tetrahydrophthalimide

Ausbeute 79.2%

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwhile heating
2. 2
   Temperaturunder refluxing
3. 3
   SonstigeAfter completion of the reaction
4. 4
   Extraktionextracted with ethyl acetate (100 ml×3 times)
5. 5
   WaschenThe organic layer was washed with an aqueous solution of sodium carbonate and water
6. 6
   Sonstigedried
7. 7
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
8. 8
   SonstigeThe resulting oily substance was purified by silica gel column chromatography (development solvent: ethyl acetate/hexane=1/5)

Vorschrift

A solution of 2-fluoro-4-chloro-5-methoxycarbonyloxyaniline (20.0 g, 91.1 mmol) and 3,4,5,6-tetrahydrophthalic anhydride (14.0 g, 92.0 mmol) in acetic acid (200 ml) was reacted for 5 hours while heating under refluxing. After completion of the reaction, the mixture was-cooled to room temperature, water (200 ml) was added thereto, and extracted with ethyl acetate (100 ml×3 times). The organic layer was washed with an aqueous solution of sodium carbonate and water, dried, and the solvent was distilled off under reduced pressure. The resulting oily substance was purified by silica gel column chromatography (development solvent: ethyl acetate/hexane=1/5) to obtain N-(2-fluoro-4-chloro-5-methoxycarbonyloxyphenyl)-3,4,5,6-tetrahydrophthalimide as a white solid (26.2 g, 72.1 mmol, 79.2% yield).

Quelle