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

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).

1. temperaturecooled in an ice bath
2. stirringThe resulting orange mixture was stirred at room temperature overnight
3. extractionThen it was extracted with ethyl acetate
4. washwashed with 10% aqueous sodium hydroxide solution (50 mL) solution
5. washOrganic layer was washed with saturated aqueous sodium chloride solution
6. concentrationconcentrated under vacuum

ORD-Eintrag

ord-1317407172cc47b997de539cdb6dbe3f

Quelldatensatz

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09073929B2