반응 #304323

반응 방정식

sodium hydride

5-bromo-1,3-difluoro-2-nitro-benzene

pyrazole

→

title compound

수율 86.0%

1-(5-Bromo-3-fluoro-2-nitro-phenyl)-1H-pyrazole

수율 86.0%

용매

THF

THF

THF

반응 조건

후처리

1. 1
   workup.STIRRINGThe resulting mixture was stirred at 0° C. for 5 minutes
2. 2
   workup.STIRRINGThe mixture was stirred at room temperature for 1 hour
3. 3
   기타quenched by addition of water (1 mL)
4. 4
   기타partitioned between water (20 mL) and ethyl acetate (50 mL)
5. 5
   세척The organic layer was washed with brine
6. 6
   건조dried (MgSO4)
7. 7
   농축concentrated in vacuo
8. 8
   기타The residue was purified by column chromatography over silica gel
9. 9
   세척eluted with ethyl acetate:hexanes (1:6)

실험 절차

To a suspension of sodium hydride (44 mg, 1.1 mmol, 60% oil dispersion) in THF (4 mL), stirred at 0° C., was added a solution of pyrazole (72 mg, 1.05 mmol) in THF (1 mL). The resulting mixture was stirred at 0° C. for 5 minutes and a solution of 5-bromo-1,3-difluoro-2-nitro-benzene (238 mg, 1 mmol) in THF (1 mL) was added. The mixture was stirred at room temperature for 1 hour, quenched by addition of water (1 mL), then partitioned between water (20 mL) and ethyl acetate (50 mL). The organic layer was washed with brine, dried (MgSO4), and concentrated in vacuo. The residue was purified by column chromatography over silica gel eluted with ethyl acetate:hexanes (1:6), to afford 240 mg (86%) of the title compound. 1H NMR (CDCl3) δ 6.55 (t, 1H), 7.45 (d, 1H), 7.60 (s, 1H), 7.80 (m, 2H). MS M+1 287, M+1+2 289.

출처