반응 #88095

반응 방정식

1-(2-fluoro-phenyl)-5-(4-nitro-phenyl)-1H-pyrazole

intermediate B

1-(2-fluoro-phenyl)-5-(4-nitro-phenyl)-1H-pyrazole

2-(4-fluoro-phenyl)-acetonitrile

sodium hydroxide

MeOH

→

title compound

수율 70.0%

3-(4-Fluoro-phenyl)-5-[2-(2-fluoro-phenyl)-2H-pyrazol-3-yl]-benzo[c]isoxazole

수율 70.0%

용매

water

반응 조건

후처리

1. 1
   workup.STIRRINGto stir for 2 h at 60° C
2. 2
   추출extracted with diethyl ether (2×40 ml)
3. 3
   세척The combined organic layers were washed with brine (30 ml)
4. 4
   건조dried (MgSO4)
5. 5
   기타evaporated
6. 6
   기타The crude product was further purified by column chromatography on silica gel (toluene/ethyl acetate 95:5)
7. 7
   기타followed by crystallization (ethyl acetate/heptane)

실험 절차

A mixture of sodium hydroxide (282 mg, 7.06 mmol) and MeOH (2.5 ml) was allowed to stir for 1 h at room temperature, 1-(2-fluoro-phenyl)-5-(4-nitro-phenyl)-1H-pyrazole (intermediate B) (200 mg, 706 μmol) and commercially available 2-(4-fluoro-phenyl)-acetonitrile (143 mg, 127 μl, 1.06 mmol) were added, and the reaction mixture was allowed to stir for 2 h at 60° C. The reaction mixture was poured into water (20 ml) and extracted with diethyl ether (2×40 ml). The combined organic layers were washed with brine (30 ml), dried (MgSO4) and evaporated. The crude product was further purified by column chromatography on silica gel (toluene/ethyl acetate 95:5) followed by crystallization (ethyl acetate/heptane) to yield the title compound as a light yellow solid (184 mg, 70%), MS (ISP) m/z=374.1 [(M+H)+], mp 171° C.

출처