Reacción #4862

Ecuación de reacción

2-bromo-m-xylene

N-allylphthalimide

acetate

triphenylphosphine

→

2-[3-(2,6-dimethylphenyl)-2-propenyl]-1H-isoindole-1,3(2H)-dione

Disolventes

triethylamine

ether

water

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe aqueous layer was separated
2. 2
   Lavadothe organic washed twice with 100 ml portions of 2N HCl
3. 3
   FiltraciónAfter filtering the organic phase
4. 4
   Lavadowashing with saturated KHCO3 and brine
5. 5
   Secadodrying over MgSO4, it
6. 6
   Concentraciónwas concentrated on the steam bath
7. 7
   OtroThe resulting solid product was purified by flash chromotography

Procedimiento

A mixture 9.3 g (50 mmole) of 2-bromo-m-xylene, 15.0 g (80 mmole) of N-allylphthalimide, 0.56 (2.5 mmole) of paladium acetate and 1.44 (5.5 mmole) of triphenylphosphine were dissolved in 111 ml of triethylamine. The solution was placed in a sealed container and heated at 100° C. for 24 hours. The reaction was then diluted with 800 ml of ether and 200 ml of water. The aqueous layer was separated and the organic washed twice with 100 ml portions of 2N HCl. After filtering the organic phase, washing with saturated KHCO3 and brine, and drying over MgSO4, it was concentrated on the steam bath. The resulting solid product was purified by flash chromotography and used in subsequent reactions.

Fuente