Dichloromethane → (4-Methylphenyl)(4'-isobutylphenyl)iodonium phenylmethylsulfate

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Reaction Steps

1.03 g of the crude tetramethylammonium phenylmethylsulfate are dissolved in 10 ml of water. 1.48 g of the crude (4-methylphenyl)(4′-isobutylphenyl)iodonium hydrogensulfate (obtained according to example 7.1), dissolved in 10 ml of methanol, are added to the solution. The mixture is stirred for 1 hour at room temperature. 10 ml of methylene chloride are added to the solution and stirred for additonal 3 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 1.31 g of (4-methylphenyl)(4′-isobutylphenyl)iodonium phenylmethylsulfate as a pale brown resin. The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ [ppm]: 0.86 (d, 6H), 1.80-1.85 (m, 1H), 2.36 (s, 3H), 2.45 (d, 2H), 4.97 (s, 2H), 7.12-7.37 (m, 9H), 7.77-7.81 (m, 4H).

Provenance & Evidence