Dimethylformamide → 3-(4-Bromobenzyl)-5-chloro-2-phenyl-3H-imidazole-4-carbaldehyde

Participants

Reaction Steps

A solution of 8.0 g (32.0 mmol) of 4-chloro-5-formyl-2-phenylimidazole (prepared according to Chem. Pharm. Bull. 24 (1976) 960-969) and 5.3 g (32.0 mmol) of K2CO3 in 200 ml of abs. DMF was stirred at RT for 20 min. A solution of 9.6 g (32.0 mmol) of 4-bromobenzyl bromide in 200 ml of abs. DMF was then added dropwise and the reaction solution was stirred at RT for 6 h. It was concentrated in vacuo, and the residue obtained was taken up in EA, washed with water, 10% strength KHSO4, 10% strength NaHCO3, and satd sodium chloride solution, and dried over Na2SO4. Chromatographic purification on SiO2 using EA/heptane (1:4) as eluent of the residue which remained after stripping off the EA yielded 11.5 g of the title compound in the form of a beige solid.

Provenance & Evidence