反应详情

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%).

1. temperaturethen cooled
2. extractionThe residue was extracted with dichloromethane
3. washthe combined organic extracts were washed with excess 5% aqueous sodium metabisulphite
4. customto remove iodine
5. dry with materialThe organic solution was dried (Na2SO4)
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by flash chromatography (gradient elution with hexane:ethyl acetate 20:1 to 10:1)