반응 #90311

반응 방정식

3-Bromo-1-(4-isopropoxyphenyl)-1H-1,2,4-triazole

cesium carbonate

1-iodo-4-(trifluoromethyl)benzene

→

title compound

수율 64.0%

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

수율 64.0%

용매

dimethylsulfoxide

반응 조건

후처리

1. 1
   기타the solution was degassed with nitrogen for 10 minutes
2. 2
   온도After cooling to room temperature
3. 3
   workup.ADDITIONthe reaction mixture was diluted with ethyl acetate
4. 4
   여과filtered through Celite®
5. 5
   여과The resulting filter cake
6. 6
   세척was rinsed with additional ethyl acetate (100 mL)
7. 7
   workup.ADDITIONSaturated aqueous ammonium chloride was added to the filtrate which
8. 8
   기타The layers were separated
9. 9
   추출the aqueous layer was extracted with ethyl acetate (2×50 mL)
10. 10
    건조The combined organic extracts were dried over anhydrous magnesium sulfate
11. 11
    농축concentrated onto Celite®
12. 12
    기타Purification by silica gel chromatography

실험 절차

3-Bromo-1-(4-isopropoxyphenyl)-1H-1,2,4-triazole (7.15 g, 48.3 mmol), copper(I) iodide (1.25 g, 6.56 mmol), cesium carbonate (18.9 g, 58.0 mmol), and 1-iodo-4-(trifluoromethyl)benzene (8.29 g, 30.5 mmol) were added to dimethylsulfoxide (50 mL) and the solution was degassed with nitrogen for 10 minutes. The solution was heated at 100° C. for 20 hours. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and filtered through Celite®. The resulting filter cake was rinsed with additional ethyl acetate (100 mL). Saturated aqueous ammonium chloride was added to the filtrate which was then stirred for 30 minutes. The layers were separated and the aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic extracts were dried over anhydrous magnesium sulfate and concentrated onto Celite®. Purification by silica gel chromatography using 0-100% ethyl acetate/hexanes as eluent provided the title compound as a white solid (5.64 g, 64%): mp 87-89° C.; 1H NMR (400 MHz, CDCl3) δ 8.53 (s, 1H), 7.85-7.77 (m, 4H); ESIMS m/z 292.0 ([M+H]+).

출처