Sulfuric Acid → 3,5-diiodonitrobenzene

Participants

Reaction Conditions

Reaction Steps

13.8 g (0.2 M) of sodium nitrite was added portionwise slowly to 96 mL of conc. sulfuric acid at 0° C. The resulting thick mixture was stirred at 0° C. for 10 minutes. A suspension of 68.25 g (0.175 M) of finely powdered 4-nitro-2,6-diiodoaniline in 175 mL of glacial acetic acid was added cautiously portionwise to the above mixture at 0° C. After the addition, the mixture was stirred 30 mins. The resulting slurry was then added slowly to a vigorously stirred suspension of 4 g of cuprous oxide in 420 mL of absolute ethanol over a period of 25 mins. Vigorous effervescence was observed during this addition. The resulting mixture was stirred 20 mins. at room temperature and then heated to reflux for 30 minutes. After cooling, this reaction mixture was poured onto a large amount of ice. The solid which separated was filtered, and washed with water. This solid was dissolved in a minimum amount of chloroform, dried over anhyd. magnesium sulfate, and the solvent was removed to give 62 g of 3,5-diiodnitrobenzene as a yellow solid. ##STR135##

Provenance & Evidence