Methyl iodide → 2-(3-Hexyl-phenyl)-4,5-diiodo-1-methyl-1H-imidazole

Participants

Reaction Steps

A solution of 8.45 g (17.6 mmol) of 2-(3-hexyl-phenyl)-4,5-diiodo-1H-imidazole in 150 ml of DMF was treated at 0° C. with 0.806 g (18.5 mmol) of sodium hydride (55% dispersion in mineral oil); 15 min later, a solution of 1.52 ml=3.47 g (24.2 mmol) of iodomethane in 25 ml of DMF was added drop by drop at 0° C. After 2 hours, the reaction mixture was poured into crashed ice and extracted twice with EtOAc; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (n-heptane/EtOAc 1:0 to 4:1) to give 7.52 g (87%) of the title compound as light red oil. MS: 495.1 (MH+).

Provenance & Evidence