반응 #607398

반응 방정식

3-(4-nitrophenyl)-1H-1,2,4-triazole

1-bromo-4-(trifluoromethyl)benzene

cesium carbonate

8-hydroxyquinoline

→

title compound

수율 63.0%

3-(4-nitrophenyl)-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazole

수율 63.0%

용매

N,N′-dimethylformamide water

반응 조건

후처리

1. 1
   온도The reaction was cooled to room temperature (about 22° C.)
2. 2
   기타quenched with ammonium hydroxide (10 mL)
3. 3
   추출The reaction mixture was extracted with ethyl acetate
4. 4
   기타The organic layer was separated
5. 5
   세척washed with water (3×100 mL) and brine (300 mL)
6. 6
   기타The organic layer was separated
7. 7
   건조dried over sodium sulfate
8. 8
   여과filtered
9. 9
   농축concentrated
10. 10
    기타Purification by flash column chromatography (silica gel)

실험 절차

A mixture of 3-(4-nitrophenyl)-1H-1,2,4-triazole (20.0 g, 105 mmol), 1-bromo-4-(trifluoromethyl)benzene (28.0 g, 124 mmol), cesium carbonate (68.4 g, 210 mmol), copper(I) iodide (2.59 g, 13.6 mmol), and 8-hydroxyquinoline (1.80 g, 12.4 mmol) in N,N′-dimethylformamide/water (9:1, 142 mL) under nitrogen was heated to 140° C. for 18 hours. The reaction was cooled to room temperature (about 22° C.) and quenched with ammonium hydroxide (10 mL). The reaction mixture was extracted with ethyl acetate. The organic layer was separated and washed with water (3×100 mL) and brine (300 mL). The organic layer was separated and dried over sodium sulfate, filtered, and concentrated. Purification by flash column chromatography (silica gel) using 0-65% ethyl acetate/petroleum ether as eluent provided the title compound as a white solid (22.0 g, 63%): 1H NMR (300 MHz, CDCl3) δ 8.72 (s, 1H), 8.42-8.34 (m, 4H), 7.94 (d, J=8.7 Hz, 2H), 7.84 (d, J=8.5 Hz, 2H); ESIMS m/z 335 ([M+H]+).

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