2-Iodotoluene → 1-[2-(Benzenesulfonyl)ethenyl]-2-methylbenzene

Participants

Reaction Conditions

Reaction Steps

To 0.186 g (1.0 mmol) of 2-(phenylsulfonyl)ethanol, 3 ml of acetonitrile was added, followed by 0.19 g (1.1 mmol) of methanesulfonic anhydride and 0.56 ml (4.0 mmol) of triethylamine, and the mixture was stirred for 5 hours at the internal temperature of 50° C. Subsequently, 0.19 ml (1.5 mmol) of o-iodotoluene, 0.11 g (0.05 mmol) of palladium acetate, and 0.067 g (0.22 mmol) of tri(o-tolyl)phosphine were added thereto, and the mixture was then refluxed for 16 hours. After cooled to room temperature, the reaction mixture was concentrated and purified by column chromatography (hexane/ethyl acetate=80/20) to obtain 0.21 g of [2-(phenylsulfonyl)ethenyl]-2-methylbenzene. Yield: 80%.

Provenance & Evidence