反应 #59100

反应方程式

KHMDS

bromide

1-(2-fluoro-5-nitrophenyl)ethanone

→

1-fluoro-4-nitro-2-(prop-1-en-2-yl)benzene

溶剂

toluene

THF

THF

反应条件

后处理

1. 1
   温度then cooled a second time to −78° C
2. 2
   其他Resulting mixture
3. 3
   温度to warm to room temperature
4. 4
   其他Solvent is then removed under reduced pressure, cyclohexane
5. 5
   workup.ADDITIONis then added
6. 6
   温度mixture heated briefly
7. 7
   温度to reflux
8. 8
   温度cooled to room temperature
9. 9
   过滤filtered
10. 10
    浓缩filtrate concentrated
11. 11
    其他Crude product is purified

实验过程

KHMDS(1 eq) in toluene is added dropwise over 5 minutes to a stirred suspension of triphenylphosphinemethyl bromide(1.2 eq) in THF at −78° C. under nitrogen. After complete addition solution is allowed to warm to room temperature for 5 minutes then cooled a second time to −78° C. 1-(2-fluoro-5-nitrophenyl)ethanone(1 eq) in THF is then added via cannulla into the cold suspension over 10 minutes. Resulting mixture is then allowed to warm to room temperature and stirred for 1 h. Solvent is then removed under reduced pressure, cyclohexane is then added and mixture heated briefly to reflux, cooled to room temperature, filtered and filtrate concentrated. Crude product is purified using flash chromatography(85% Hex:15% EtoAc) on silica to afford 1-fluoro-4-nitro-2-(prop-1-en-2-yl)benzene.

来源