General procedure: 1-fluoro-4-nitrobenzene (10 g, 70.9 mmol), 2-methyl-1H-imidazole (5.8 g, 70.9 mmol) and cesium carbonate (Cs2CO3, 34.7 g, 106.4 mmol) were placed in degassed N,N-dimethylformamide (DMF, 200 mL). The mixture was heated to 100 °C and stirred overnight under nitrogen protection. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming the complete consumption of 1-fluoro-4-nitrobenzene, the reaction mixture was concentrated under reduced pressure. Water (300 mL) was added to the concentrated residue and a gray precipitate was precipitated, which was separated by filtration to afford the target compound 2-methyl-1-(4-nitrophenyl)-1H-imidazole (12.8 g, 89% yield).
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