4-Nitrobenzyl bromide → HCID 13646840, compound

Participants

Reaction Steps

To a solution of 2 g (8.1×10-3 moles) of i-propyl ester of 2-bromo-4-methyl-5-imidazolecarboxylic acid in 20 ml of benzene was added 1.2 ml (8.1×10-3 moles) of diazabicycloundecane, followed by 1.7 g (8.1×10-3 moles) of p-nitrobenzylbromide. The resulting mixture was heated to reflux overnight, cooled to room temperature and filtered. Concentration in vacuo gave a golden oil. This residue was purified by medium pressure liquid chromatography on silica gel to yield 2.1 g (70%) i-propyl 1-(4-nitrobenzyl)-2-bromo-4-methyl-5-imidazolecarboxylate as a yellow oil and 600 mg (20%) of the desired product, i-propyl 2-bromo-3-(4-nitrobenzyl)-4-methyl-5-imidazolecarboxylate also a yellow oil.

Provenance & Evidence