Potassium Iodide → HCID 18319289, compound

Participants

Reaction Steps

A suspension of 4-amino-l-(3-cyanophenyl)-2-methylbenzene (2.5 gm, 12.0 mmol) in conc. hydrochloric acid (13 mL) and water (16 mL) at 0° C., was treated with a solution of sodium nitrite (1.83 gm, 26.5 mmol) in water (10 mL) over 10 mins. The mixture was stirred for 20 mins and then a solution of potassium iodide (8.40 gm, 50.6 mmol) in water (20 mL) was added over 10 mins. The resultant mixture was heated at 80° C. for 2 h then cooled. The residue was extracted with dichloromethane and the combined organic extracts were washed with excess 5% aqueous sodium metabisulphite, 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-(3-cyanophenyl)-4-iodo-2-methylbenzene as a white solid (1.105 gm, 29%).

Provenance & Evidence