반응 #45622

반응 방정식

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

potassium carbonate

potassium carbonate

→

compound

수율 64.0%

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

수율 64.0%

용매

N,N-dimethylformamide

water

methanol

water

methanol

N,N-dimethylformamide

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   workup.ADDITIONwas added
3. 3
   추출followed by extraction with ethyl acetate
4. 4
   세척The organic layer was washed with saturated brine
5. 5
   건조dried over anhydrous sodium sulfate
6. 6
   기타the 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
    추출followed by extraction with ethyl acetate
11. 11
    세척The organic layer was washed with saturated brine
12. 12
    건조dried over anhydrous sodium sulfate
13. 13
    기타the solvent was evaporated away
14. 14
    세척The precipitated solid was washed with a mixed solvent of ethyl acetate/isopropyl ether
15. 15
    여과collected by filtration

실험 절차

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.

출처