Sulfuric Acid → (4-Methylphenyl)(4'-isobutylphenyl)iodonium hydrogensulfate

Participants

Reaction Steps

11.9 g (54.8 mmol) of 4-iodotoluene and 9.2 g (68.5 mmol) of isobutylbenzene are added dropwise to a solution of 35 ml of conc. sulfuric acid and 22 ml of water under cooling by an ice bath. 25 g of ammonium peroxodisulfate are added by portions to the solution under cooling by an ice-salt bath, keeping the temperature below 0° C. for 1 hour. The reaction mixture is stirred overnight and the temperature is gradually raised to room temperature during the course of the reaction. After cooling the reaction mixture by ice an bath, 118 ml of water are added. The product is extracted with methylene chloride, and the organic layer is washed with water, dried over MgSO4, and concentrated, yielding (4-methylphenyl)(4′-isobutylphenyl)iodonium hydrogensulfate as a brown solid. The crude (4-methylphenyl)(4′-isobutylphenyl)iodonium hydrogensulfate is used in the next step without further purification.

Provenance & Evidence