Reacción #90311

Ecuación de reacción

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

cesium carbonate

1-iodo-4-(trifluoromethyl)benzene

→

title compound

Rendimiento 64.0%

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

Rendimiento 64.0%

Disolventes

dimethylsulfoxide

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe solution was degassed with nitrogen for 10 minutes
2. 2
   TemperaturaAfter cooling to room temperature
3. 3
   workup.ADDITIONthe reaction mixture was diluted with ethyl acetate
4. 4
   Filtraciónfiltered through Celite®
5. 5
   FiltraciónThe resulting filter cake
6. 6
   Lavadowas rinsed with additional ethyl acetate (100 mL)
7. 7
   workup.ADDITIONSaturated aqueous ammonium chloride was added to the filtrate which
8. 8
   OtroThe layers were separated
9. 9
   Extracciónthe aqueous layer was extracted with ethyl acetate (2×50 mL)
10. 10
    SecadoThe combined organic extracts were dried over anhydrous magnesium sulfate
11. 11
    Concentraciónconcentrated onto Celite®
12. 12
    OtroPurification by silica gel chromatography

Procedimiento

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]+).

Fuente