Sodium Carbonate → 2-(4-Trifluoromethoxyphenyl)selenophene

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Reaction Steps

A mixture of 15.1 g (58.7 mmol) of 2-iodoselenophene, 13.9 g (67.7 mmol) of 4-trifluoromethoxyphenylboronic acid, 3.90 g (3.38 mmol) of tetrakis(triphenylphosphine)palladium(0) and 150 ml of 2 N sodium carbonate soln. in 400 ml of toluene/ethanol (1:1) is heated under reflux for 23 h. After cooling, the organic phase is separated off, and the aqueous phase is extracted a number of times with MTBE. The combined organic phases are washed with 1 N hydrochloric acid and sat. sodium chloride soln. The solution is dried using sodium sulfate and concentrated to dryness. The residue is purified by column chromatography (SiO2, n-heptane:EtOAc=20:1→10:1→1:1). Further purification is carried out by recrystallisation from n-heptane; 2-(4-trifluoromethoxyphenyl)selenophene is obtained as a yellowish solid.

Provenance & Evidence