反应 #90311

反应方程式

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

cesium carbonate

1-iodo-4-(trifluoromethyl)benzene

→

title compound

收率 64.0%

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

收率 64.0%

溶剂

dimethylsulfoxide

反应条件

后处理

1. 1
   其他the solution was degassed with nitrogen for 10 minutes
2. 2
   温度After cooling to room temperature
3. 3
   workup.ADDITIONthe reaction mixture was diluted with ethyl acetate
4. 4
   过滤filtered through Celite®
5. 5
   过滤The resulting filter cake
6. 6
   洗涤was rinsed with additional ethyl acetate (100 mL)
7. 7
   workup.ADDITIONSaturated aqueous ammonium chloride was added to the filtrate which
8. 8
   其他The layers were separated
9. 9
   萃取the aqueous layer was extracted with ethyl acetate (2×50 mL)
10. 10
    干燥The combined organic extracts were dried over anhydrous magnesium sulfate
11. 11
    浓缩concentrated onto Celite®
12. 12
    其他Purification by silica gel chromatography

实验过程

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]+).

来源