反应详情

A mixture of 8.9 g (42.4 mmol) of 2-bromoselenophene, 16.0 g (59.7 mmol) of 4-(4-ethylcyclohexyl)-2,3-difluorophenylboronic acid, 3.93 g (3.40 mmol) of tetrakis(triphenylphosphine)palladium(0) and 125 ml of 2 N sodium carbonate soln. in 600 ml of toluene/ethanol (1:1) is heated under reflux for 20 h. After cooling, the organic phase is separated off, and the aqueous phase is extracted with toluene. The combined organic phases are washed with sat. sodium chloride soln., and the solution is dried using sodium sulfate. The solution is concentrated to dryness, and the residue is purified by column chromatography (SiO2, toluene). The further purification is carried out by recrystallisation from n-heptane:EtOH=1:1 and IPA. 2-[4-(4-Ethylcyclohexyl)-2,3-difluorophenyl]selenophene is obtained as a pale-yellowish solid.

1. temperatureunder reflux for 20 h
2. temperatureAfter cooling
3. customthe organic phase is separated off
4. extractionthe aqueous phase is extracted with toluene
5. washThe combined organic phases are washed with sat. sodium chloride soln
6. custom, and the solution is dried
7. concentrationThe solution is concentrated to dryness
8. customthe residue is purified by column chromatography (SiO2, toluene)
9. customThe further purification
10. customis carried out by recrystallisation from n-heptane