Imidazole → (4-Iodobutyl)benzene

Participants

Reaction Steps

To a mixture of 4-phenyl-1-butanol (601 mg, 4.0 mmol), Ph3P (1.57 g, 6.0 mmol, 1.5 equiv.) and imidazole (409 mg, 6.0 mmol, 1.5 equiv.) in toluene (20 mL) was added I2 (1.52 g, 6.0 mmol, 1.5 equiv.) at 0° C. The mixture was allowed to stand overnight, and the reaction was quenched with saturated Na2S2O3 solution. The mixture was extracted with hexane/EtOAc 10:1, and the organic layer was washed with brine and dried over Na2SO4. After concentration, the residue was filtrated through Celite, and the Celite was washed with hexane. After removal of the solvent, (4-iodobutyl)benzene (1.04 g, 100%) was obtained as a pale yellow oil, which was used in the subsequent step without purification.

Provenance & Evidence