Реакция #90311

Уравнение реакции

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

cesium carbonate

1-iodo-4-(trifluoromethyl)benzene

→

title compound

Выход 64.0%

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

Выход 64.0%

Растворители

dimethylsulfoxide

Условия реакции

Обработка

1. 1
   Другоеthe solution was degassed with nitrogen for 10 minutes
2. 2
   ТемператураAfter cooling to room temperature
3. 3
   workup.ADDITIONthe reaction mixture was diluted with ethyl acetate
4. 4
   Фильтрацияfiltered through Celite®
5. 5
   ФильтрацияThe resulting filter cake
6. 6
   Промывкаwas rinsed with additional ethyl acetate (100 mL)
7. 7
   workup.ADDITIONSaturated aqueous ammonium chloride was added to the filtrate which
8. 8
   ДругоеThe layers were separated
9. 9
   Экстракцияthe aqueous layer was extracted with ethyl acetate (2×50 mL)
10. 10
    СушкаThe combined organic extracts were dried over anhydrous magnesium sulfate
11. 11
    Концентрированиеconcentrated onto Celite®
12. 12
    ДругоеPurification by silica gel chromatography

Методика

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]+).

Источник