Methane → 1-(3-nitrophenyl)-1H-imidazole

Participants

Reaction Conditions

Reaction Steps

An intimate mixture of 1-iodo-3-nitrobenzene (24.9 g, 0.1 mol), copper bronze (320 mg, 5 mmol), potassium carbonate (15.2 g, 0.11 mol) and imidazole (15.0 g, 0.22 mol) was heated under a stream of nitrogen at 200° C. for 90 minutes. The reaction was cooled to 100° C., carefully treated with water (750 ml) and the resulting suspension stirred to ambient temperature over 16 hours. Filtration gave a grey-coloured solid which was dissolved in hot toluene (125 ml) and treated with decolourising charcoal (2 g). Filtration and cooling afforded 1-(3-nitrophenyl)-1H-imidazole as pale green needles (13.5 g, 71%). δH (360 MHz, CDCl3) 7.29 (1H, br s), 7.38 (1H, br s), 7.68-7.78 (2H, m), 7.97 (1H, br s), 8.23-8.29 (2H, m).

Provenance & Evidence