Reacción #1528385

Ecuación de reacción

imidazole

potassium hydroxide

α,α′-dibromo-m-xylene

→

1-[3-(1H-imidazole-1yl-methyl)benzyl]-1H-imidazole

Rendimiento 63.9%

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroTo a 500 mL round bottom flask equipped with a stirbar
2. 2
   FiltraciónThe cloudy solution was filtered
3. 3
   Lavadothe white solids rinsed with acetone
4. 4
   OtroThe resulting filtrate was dried on silica
5. 5
   Otropartitioned on a silica gel column
6. 6
   OtroThe product fractions were evaporated of solvent
7. 7
   Otrothe resulting oil recrystallized from ethyl acetate/hexanes

Procedimiento

To a 500 mL round bottom flask equipped with a stirbar was added 11.6 g imidazole (170 mmol) and 9.55 g (170 mmol) finely pulverized potassium hydroxide. These were stirred in 200 mL acetone until the solution became yellow translucent. 15.0 g (56.8 mmol) α,α′-dibromo-m-xylene was then added, and the solution was stirred at room temperature overnight. The cloudy solution was filtered, and the white solids rinsed with acetone. The resulting filtrate was dried on silica and partitioned on a silica gel column using 30/70 acetonitrile/methanol as eluent. The product fractions were evaporated of solvent and the resulting oil recrystallized from ethyl acetate/hexanes to give 8.65 g 1-[3-(1H-imidazole-1yl-methyl)benzyl]-1H-imidazole as a white solid.

Fuente