Potassium Iodide → HCID 18319225, compound

Participants

Reaction Steps

A suspension of 4-amino-1-(4-cyanophenyl)-2-methylbenzene (250 mg 1.2 mmol) in conc. hydrochloric acid (1.3 mL) and water (1.6 mL) at 0° C., was treated with a solution of sodium nitrite (183 mg, 2.65 mmol) in water (1 mL) over 10 mins. The mixture was stirred for 20 mins and then a solution of potassium iodide (840 mg, 5.06 mmol) in water (2 mL) was added, over 10 mins. The resultant mixture was heated at 90° C. for 2 h, then cooled. The residue was extracted with dichloromethane (3×30 mL) and the combined organic extracts were washed with 5% aqueous sodium metabisulphite (4×30 mL), to remove iodine. The organic solution was dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (gradient elution with hexane:ethyl acetate 20:1 to 10:1) to give 1-(4-cyanophenyl)-4-iodo-2-methylbenzene as a white solid (263 mg, 69%).

Provenance & Evidence