Reaktion #1528384

Reaktionsgleichung

benzimidazole

potassium hydroxide

α,α′-dibromo-m-xylene

→

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

Ausbeute 18.8%

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo a 1 L round bottom flask equipped with a stirbar
2. 2
   Temperaturat reflux
3. 3
   Temperaturat reflux for 6 hours
4. 4
   Sonstigefollowed by room temperature
5. 5
   workup.STIRRINGstirring for 72 hours
6. 6
   FiltrationThe cloudy solution was filtered
7. 7
   Waschenthe white solids rinsed with acetone
8. 8
   SonstigeThe resulting filtrate was dried on silica
9. 9
   Sonstigepartitioned on a silica gel column
10. 10
    SonstigeThe product fractions were evaporated of solvent

Vorschrift

To a 1 L round bottom flask equipped with a stirbar was added 26.8 g benzimidazole (227 mmol) and 12.7 g (227 mmol) finely pulverized potassium hydroxide. These were stirred in 500 mL acetone for 20 minutes at reflux. 20.0 g (78.5 mmol) α,α′-dibromo-m-xylene was then added, and the solution was stirred at reflux for 6 hours followed by room temperature stirring for 72 hours. 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 a gradient of 100% acetonitrile→90% acetronitrile/10% MeOH as eluent. The product fractions were evaporated of solvent to give 5 g 1-[3-(1H-benzimidazole-1yl-methyl)benzyl]-1H-benzimidazole as a white solid.

Quelle