Synthesis
A mixture of 2-bromo-1-(4-fluorophenyl)ethanone (10.9 g, 50 mmol) and formamide (14 mL, 350 mmol) was stirred at 170 C and under nitrogen for 4 hours. The reaction mixture was cooled and mixed with ethyl acetate (40 mL). Saturated aqueous sodium bicarbonate (50 mL) was carefully added while the mixture was cooled in an ice water bath. The aqueous layer was separated and extracted with ethyl acetate (2 x 40mL). The combined organic solutions were washed with water (30 mL) and brine (30 mL), dried (Na2SO 4) and concentrated. Rapid chromatography on silica gel (10-100% hexane solution of ethyl acetate) yielded 4-(4-fluorophenyl)-1H-imidazole (3.46 g, 21 mmol, 43% yield) as a solid.
