Reaktion #590348

Reaktionsgleichung

carbon monoxide

2-acetylamino-4-fluoro-5-iodo-benzoic acid ethyl ester

potassium carbonate

3-fluorophenyl-boronic acid

carbon monoxide

→

title compound

Ausbeute 29.1%

2-Acetylamino-4-fluoro-5-(3-fluoro-benzoyl)-benzoic acid ethyl ester

Ausbeute 29.1%

Lösungsmittel

anisole

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Extraktionthe mixture was extracted with ethyl acetate
3. 3
   WaschenThe resulting organic layer was washed with brine
4. 4
   Trocknendried over magnesium sulfate
5. 5
   Sonstigethe solvent was evaporated
6. 6
   SonstigeThe residue was purified
7. 7
   Sonstigeseparated by silica gel column chromatography (ethyl acetate:hexane=1:5)

Vorschrift

A total of 812 mg of 2-acetylamino-4-fluoro-5-iodo-benzoic acid ethyl ester obtained in Production Example II-7-c was dissolved in 13.9 ml of anisole, and 956 mg of potassium carbonate, 356 mg of 3-fluorophenyl-boronic acid and 49 mg of bis(triphenylphosphine)palladium dichloride were added. After replacing the inside atmosphere of the reaction system with carbon monoxide gas, the mixture was stirred at 80° C. in an atmosphere of carbon monoxide (normal pressure) for 14 hours. After cooling to room temperature and replacing the inside atmosphere of the reaction system with nitrogen gas, water was added and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with brine, dried over magnesium sulfate and the solvent was evaporated. The residue was purified and separated by silica gel column chromatography (ethyl acetate:hexane=1:5), to give 234 mg of the title compound as pale yellow crystals.

Quelle