反应详情

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.

1. temperaturethen cooled a second time to 78° C
2. customResulting mixture
3. temperatureto warm to room temperature
4. customSolvent is then removed under reduced pressure, cyclohexane
5. additionis then added
6. temperaturemixture heated briefly
7. temperatureto reflux
8. temperaturecooled to room temperature
9. filtrationfiltered
10. concentrationfiltrate concentrated
11. customCrude product is purified