Dichloromethane → Di(4-tert-amylphenyl)iodonium propylsulfate

Participants

Reaction Steps

3.4 g of the crude tetramethylammonium propylsulfate are dissolved in 10 ml of water. To the solution are added 6.8 g of the crude di(4-tert-amylphenyl)iodonium hydrogensulfate prepared according to the method of example 3.1, dissolved in 5 ml of methanol. The mixture is stirred for 4 hours at room temperature. 10 ml of methylene chloride are added to the solution and stirred for additonal 2 hours at room temperature. The product is extracted with methylene chloride and the organic layer is washed with water, dried over MgSO4, and concentrated. The residue is purified by flash chromatography on silica gel with methylene chloride, followed by methylene chloride and ethanol (95:5) as an eluent, yielding 3.86 g of di(4-tert-amylphenyl)iodonium propylsulfate as a brownish solid, mp. 48-53° C. The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ [ppm]: 0.65 (t, 6H), 0.88 (t, 3H), 1.24 (s, 12H), 1.56-1.66 (m, 6H), 3.89 (t, 2H), 7.37 (d, 4H), 7.88 (d, 4H).

Provenance & Evidence