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

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Reaction Steps

3.9 g of crude tetramethylammonium phenylsulfate prepared according to the method of Example 1.2 are dissolved in 10 ml of water. To the solution 6.8 g of the crude di(4-tert-amylphenyl)iodonium hydrogensulfate, dissolved in 5 ml of methanol, are added. The mixture is stirred for 3 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. 200 ml of tert-butyl methyl ether are added to the residue, affording a white solid. After the suspension is stirred at 60° C. for 15 min, the precipitate is filtered off and washed with tert-butyl methyl ether, yielding 4.37 g of di(4-tert-amylphenyl)iodonium phenylsulfate as a white solid, mp. 122-125° C. The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ [ppm]: 0.64 (t, 6H), 1.23 (s, 12H), 1.61 (q, 4H), 7.07 (t, 1H), 7.21-7.29 (m, 4H), 7.34 (d, 4H), 7.82 (d, 4H).

Provenance & Evidence