Reaktion #81324

Reaktionsgleichung

N-bromosuccinimide

benzoyl peroxide

diethyl 1-benzyl-2-methylimidazole-4,5-dicarboxylate

→

title compound

Ausbeute 74.9%

Diethyl 1-benzyl-2-bromomethylimidazole-4,5-dicarboxylate

Ausbeute 74.9%

Lösungsmittel

carbon tetrachloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenAt the end of this time, the reaction solution was washed with a 5% w/v aqueous solution of sodium thiosulfate and with a saturated aqueous solution of sodium hydrogencarbonate, in that order
2. 2
   Einengenafter which it was concentrated by evaporation under reduced pressure
3. 3
   SonstigeThe resulting residue was purified by column chromatography through silica gel
4. 4
   workup.ADDITIONby volume mixture of hexane and ethyl acetate as the eluent

Vorschrift

2.52 g of N-bromosuccinimide and 0.42 of benzoyl peroxide were added to a solution of 4.07 g of diethyl 1-benzyl-2-methylimidazole-4,5-dicarboxylate [prepared as described in step (i) above] in 80 ml of carbon tetrachloride, and the mixture was irradiated by a 375 W tungsten lamp for 50 minutes, whilst stirring. At the end of this time, the reaction solution was washed with a 5% w/v aqueous solution of sodium thiosulfate and with a saturated aqueous solution of sodium hydrogencarbonate, in that order, after which it was concentrated by evaporation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 3:2 by volume mixture of hexane and ethyl acetate as the eluent, to give 3.81 g of the title compound as a syrup.

Quelle