反应详情

A mixture of 27.9 g (0.11 mol) of 2-iodoselenophene, 15.0 g (0.11 mol) of 2-hydroxyphenylboronic acid, 6.8 g (5.88 mmol) of tetrakis(triphenylphosphine)palladium(0) and 235 ml of 2 N sodium carbonate soln. in 600 ml of toluene/ethanol (1:1) is heated under reflux for 19 h. The mixture is diluted with MTBE and washed with water. The aqueous phase is extracted with MTBE, and the combined organic phases are washed with 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:MTBE=4:1→1:1). Further purification is carried out by digestion in cold n-heptane; 4-selenophen-2-ylphenol is obtained as a beige solid.

1. temperatureunder reflux for 19 h
2. washwashed with water
3. extractionThe aqueous phase is extracted with MTBE
4. washthe combined organic phases are washed with sat. sodium chloride soln
5. customThe solution is dried
6. concentrationconcentrated to dryness
7. customThe residue is purified by column chromatography (SiO2, n-heptane:MTBE=4:1→1:1)
8. customFurther purification