[Li]CCCC.[CH2:6]([N:10]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:12]=[CH:11]1)[CH2:7][CH2:8][CH3:9].[I:21]I.[NH4+].[Cl-]>CCCCCC.C1COCC1>[CH2:6]([N:10]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:12]=[C:11]1[I:21])[CH2:7][CH2:8][CH3:9]BuLi (1.60 g) in hexane is added to a solution of 1-butyl-4-phenyl-1H-imidazole (4.16 g) in 60 mL of THF. The mixture is stirred at −78° C. for 1 hour. A solution of I2 (5.81 g) in 20 mL of THF is then added dropwise. The resulting mixture is stirred at −78° C. for 30 minutes and then warmed to room temperature. Saturated NH4Cl is added to quench the reaction. The THF is evaporated; the residue is extracted with ethyl acetate, washed with brine, and dried over Na2SO4. Concentration and purification via flash chromatography provides 1-butyl-2-iodo-4-phenyl-1H-imidazole.
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