p-Fluoronitrobenzene → ethyl 1-(4-nitrophenyl)-1H-imidazole-4-carboxylate

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Reaction Conditions

Reaction Steps

A mixture of 1H-imidazole-4-carboxylic acid ethyl ester (J.Het.Chem., 19, 253 (1982)) (584 mg, 4.17 mmol), 4-fluoronitrobenzene (588 mg, 4.17 mmol) and anhydrous sodium carbonate (487 mg, 4.59 mmol) in dry dimethylformamide (10 ml) was heated at 50° C. for 24 hours under nitrogen. After cooling to room temperature the mixture was poured into ice-cold water (60 ml) and the resulting solid collection by filtration, washed with water and dried under reduced pressure at 60° C. to give 1-(4-nitrophenyl)imidazole-4-carboxylic acid ethyl ester (980 mg, 90%) as an off-white solid, m.p. 198-200° C.

Provenance & Evidence