Reaktion #90161

Reaktionsgleichung

ethyl acetate

4-chloro-3-nitro-benzonitrile

cesium carbonate

4-(4-Ethyl-3-iodo-phenyl)-4-methyl-3-oxo-pentanoic acid tert-butyl ester

→

title compound

Ausbeute 26.0%

6-Cyano-2-[1-(4-ethyl-3-iodophenyl)-1-methyl-ethyl]-benzofuran-3-carboxylic acid tert-butyl ester

Ausbeute 26.0%

Lösungsmittel

NMP

NMP

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at 50° C. for 64 hrs under nitrogen atmosphere
2. 2
   Waschenthe organic layer was washed with saturated aqueous solution of ammonium chloride (20 ml)
3. 3
   WaschenThe organic layer was further washed with saturated brine
4. 4
   Trocknendried over sodium sulfate
5. 5
   SonstigeThe drying agent was removed by filtration
6. 6
   Sonstigethe residues obtained
7. 7
   Einengenafter concentration under reduced pressure
8. 8
   Sonstigewere purified by silica gel column chromatography (ethyl acetate/hexane)

Vorschrift

4-(4-Ethyl-3-iodo-phenyl)-4-methyl-3-oxo-pentanoic acid tert-butyl ester (1.00 g, 2.40 mmol) was dissolved in NMP (4 ml), added with cesium carbonate (1.56 g, 4.80 mmol, 2.0 eq.), and the mixture was stirred for 5 min. The NMP solution (2 ml) of 4-chloro-3-nitro-benzonitrile (542 mg, 2.88 mmol, 1.2 eq.) was added thereto, and the mixture was stirred at 50° C. for 64 hrs under nitrogen atmosphere. After cooling to room temperature, ethyl acetate (20 ml) was added and the organic layer was washed with saturated aqueous solution of ammonium chloride (20 ml). The organic layer was further washed with saturated brine and dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (white amorphous, 320 mg, 26%).

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