Reaktion #45622

Reaktionsgleichung

6-Bromo-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile

potassium carbonate

potassium carbonate

→

compound

Ausbeute 64.0%

6-Bromo-2-cyclopropyl-7-methoxy-5-methyl-1,3-benzoxazole-4-carbonitrile

Ausbeute 64.0%

Lösungsmittel

N,N-dimethylformamide

water

methanol

water

methanol

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   workup.ADDITIONwas added
3. 3
   Extraktionfollowed by extraction with ethyl acetate
4. 4
   WaschenThe organic layer was washed with saturated brine
5. 5
   Trocknendried over anhydrous sodium sulfate
6. 6
   Sonstigethe solvent was evaporated away
7. 7
   workup.ADDITIONwas added
8. 8
   workup.STIRRINGby again stirring at 60° C. for 14 hours
9. 9
   workup.ADDITIONwas added
10. 10
    Extraktionfollowed by extraction with ethyl acetate
11. 11
    WaschenThe organic layer was washed with saturated brine
12. 12
    Trocknendried over anhydrous sodium sulfate
13. 13
    Sonstigethe solvent was evaporated away
14. 14
    WaschenThe precipitated solid was washed with a mixed solvent of ethyl acetate/isopropyl ether
15. 15
    Filtrationcollected by filtration

Vorschrift

6-Bromo-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-77) (4.88 g, 16.5 mmol) was suspended in a mixed solvent of methanol (30 ml) and N,N-dimethylformamide (50 ml), potassium carbonate (4.57 g, 33.0 mmol) was added, followed by stirring at 60° C. for 30 minutes. With cooling with ice, water was added, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, the solvent was evaporated away. The residue was suspended in a mixed solvent of methanol (30 ml) and N,N-dimethylformamide (50 ml), potassium carbonate (4.57 g, 33.0 mmol) was added, followed by again stirring at 60° C. for 14 hours. With cooling with ice, water was added, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, the solvent was evaporated away. The precipitated solid was washed with a mixed solvent of ethyl acetate/isopropyl ether and collected by filtration to obtain the entitled compound (2.599 g, 64%) as a colorless solid.

Quelle