Allyl iodide → 3-(2-Ethylphenyl)-1-propene

Temperatur

50 °C

To a suspension of 8.53 g (350 mmol) of magnesium in 270 mL of dry THF was added 50 g (270 mmol) of 1-bromo-2-ethyl benzene. The temperature was maintained at 50° C. during addition, then was heated under reflux. After 1 h, the solution was cooled to -78° C. under N2, and 54.42 g (324 mmol) of allyl iodide was added dropwise. The mixture was allowed to warm to room temperature, stirred for an additional 2 h, then cooled to 0° C. The reaction was quenched by addition of 2M HCl and 500 mL of ether and the layers were separated. The organic layer was washed with 30 mL of saturated NaHCO3 solution and brine, dried over MgSO4, filtered and concentrated. The oily residue was filtered through silica gel with 20% ethyl acetate-hexane and the eluate was concentrated to afford the crude 1-allyl-2-ethylbenzene as a colorless oil.

1. temperaturewas heated
2. temperatureunder reflux
3. temperaturethe solution was cooled to -78° C. under N2
4. temperatureto warm to room temperature
5. temperaturecooled to 0° C
6. customThe reaction was quenched by addition of 2M HCl and 500 mL of ether
7. customthe layers were separated
8. washThe organic layer was washed with 30 mL of saturated NaHCO3 solution and brine
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. concentrationconcentrated
12. filtrationThe oily residue was filtered through silica gel with 20% ethyl acetate-hexane
13. concentrationthe eluate was concentrated

ORD-Eintrag

ord-5fc41e887c3041568b2ae8708bc7e2d7

Quelldatensatz

uspto-grants-2000_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06051590