Reaction #1726662

Reaction equation

1,3-diiodo-5,5-dimethylimidazolidine-2,4-dione

9-phenylanthracene

acetic acid

water

9-phenylanthracene

→

yellow solid

Yield 117.3%

9-iodo-10-phenylanthracene

Yield 117.3%

Solvents

chloroform

Conditions

Workup

1. 1
   WashThis mixture was washed with water twice
2. 2
   Extractionthe aqueous layer was extracted with chloroform
3. 3
   Washwashed with a saturated saline
4. 4
   Dryingthe organic layer was dried with magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Concentrationthe obtained filtrate was concentrated
7. 7
   Otherto give a brown solid
8. 8
   WashThis solid was washed with hexane

Procedure

Into a 500 mL Erlenmeyer flask was put 4.5 g (18 mmol) of 9-phenylanthracene. Then 200 mL of acetic acid was added to the flask, followed by heating to 70° C., and 9-phenylanthracene was dissolved therein. Into this solution, 5.2 g (13 mmol) of 1,3-diiodo-5,5-dimethylimidazolidine-2,4-dione (abbreviation: DIH) was added. This solution was stirred in air at 70° C. for 3 hours. After the stirring, about 100 mL of water and about 200 mL of chloroform were added to this solution. This mixture was washed with water twice, and the aqueous layer was extracted with chloroform. The extracted solution was combined with the organic layer and washed with a saturated saline, and then the organic layer was dried with magnesium sulfate. This mixture was gravity filtered, and the obtained filtrate was concentrated to give a brown solid. This solid was washed with hexane to give 5.8 g of a yellow solid, which was the object of the synthesis, in a yield of 86%.

Source