Potassium Iodide → 1-Chloro-2-iodo-3-nitrobenzene

Participants

Reaction Steps

2-chloro-6-nitroaniline (143-1; 1.0 g, 0.0058 mol) was dissolved in hydrochloric acid (10 mL) and cooled in an ice bath. Then a solution of sodium nitrite (0.68 g, 0.0098 mol) in water (10 mL) was added very slowly with stirring. After 15 min the reaction mixture was filtered through glass wool in to a solution of potassium iodide (4.1 g, 0.024 mol) in water (10 mL). The resulting orange mixture was stirred at room temperature overnight. Then it was extracted with ethyl acetate and washed with 10% aqueous sodium hydroxide solution (50 mL) solution. Organic layer was washed with saturated aqueous sodium chloride solution and concentrated under vacuum to obtain the title compound. 1H NMR (400 MHz, CDCl3) δ 7.854-7.835 (d, J=7.6 Hz, 1H), 7.788-7.768 (d, J=8 Hz, 1H), 7.624-7.584 (t, J=7.6 Hz, 1H).

Provenance & Evidence