Reaction #1528385

Reaction equation

imidazole

potassium hydroxide

α,α′-dibromo-m-xylene

→

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

Yield 63.9%

Solvents

acetone

Conditions

Workup

1. 1
   OtherTo a 500 mL round bottom flask equipped with a stirbar
2. 2
   FiltrationThe cloudy solution was filtered
3. 3
   Washthe white solids rinsed with acetone
4. 4
   OtherThe resulting filtrate was dried on silica
5. 5
   Otherpartitioned on a silica gel column
6. 6
   OtherThe product fractions were evaporated of solvent
7. 7
   Otherthe resulting oil recrystallized from ethyl acetate/hexanes

Procedure

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.

Source