Acetic Acid → 9-Iodo-10-phenylanthracene

Participants

Reaction Conditions

Reaction Steps

In a 500 mL Erlenmeyer flask was added 4.5 g (18 mmol) of 9-phenylanthracene. To the flask was added 200 mL of acetic acid, followed by heating at 70° C. to dissolve 9-phenylanthracene therein. To the resulting solution was added 5.2 g (13 mmol) of 1,3-diiodo-5,5-dimethylimidazolidine-2,4-dione (DIH), and the solution was stirred under air at 70° C. for 3 hours. After the reaction, ca. 100 mL of water and ca. 200 mL, of chloroform were added to this solution. The resulting mixture was washed with water twice, and the organic layer was separated from the aqueous layer. The aqueous layer was extracted with chloroform. The extract was combined with the organic layer and washed with brine, and then the combined organic layer was dried with magnesium sulfate. This mixture was gravity filtered, and the filtrate obtained was concentrated to give a brown solid. This solid was washed with hexane to give 5.8 g of a yellow solid in a yield of 86%, which was the desired substance. The synthetic scheme is shown in the following (A-2).

Provenance & Evidence