反应 #2139944

反应方程式

4-bromo-2-fluoro-1-iodobenzene

1-pentyne

water

ether

→

4-bromo-2-fluoro-1-pent-1-ynylbenzene

溶剂

THF

triethylamine

反应条件

后处理

1. 1
   workup.STIRRINGthe mixture was stirred for a further 5 minutes
2. 2
   过滤The reaction mixture was filtered through Celite® with suction
3. 3
   其他the phases were separated
4. 4
   萃取The aqueous phase was extracted twice with MTB ether
5. 5
   洗涤the combined organic phases were washed three times with water
6. 6
   干燥dried over sodium sulfate
7. 7
   其他evaporated under reduced pressure
8. 8
   过滤The crude product was filtered through silica gel with n-heptane

实验过程

190 g (0.600 mol) of 4-bromo-2-fluoro-1-iodobenzene and 65.3 ml of 1-pentyne were dissolved in a mixture of 900 ml of THF and 1.2 l of triethylamine and cooled to 10° C., and 1.14 g (6 mmol) of copper(I) iodide and 8.42 g (12 mmol) of bis(triphenylphosphine)palladium(II) chloride were added. The batch was stirred overnight at room temperature, water and MTB ether were subsequently added, and the mixture was stirred for a further 5 minutes. The reaction mixture was filtered through Celite® with suction, and the phases were separated. The aqueous phase was extracted twice with MTB ether, and the combined organic phases were washed three times with water, dried over sodium sulfate and evaporated under reduced pressure. The crude product was filtered through silica gel with n-heptane, giving 129 g of 4-bromo-2-fluoro-1-pent-1-ynylbenzene as a yellow liquid. Hydrogenation on palladium/activated carbon (10%) in THF gave 131 g (100%) of 4-bromo-2-fluoro-1-pentylbenzene as a yellow liquid.

来源