Reacción #2006420

Ecuación de reacción

Allylbenzene

4-bromobenzoic acid

Et3N

triphenylphosphine

→

mixture

Rendimiento 19.9%

4(3-Phenylpropenyl)-benzoic Acid 4-(3-Phenyl-2-propenyl)-benzoic Acid

Rendimiento 19.9%

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux overnight in a round bottom flask
2. 2
   ExtracciónAdded HCl 1N, extracted with EtOAc
3. 3
   Secadodried the organic layer on anhydrous MgSO4
4. 4
   Filtraciónfiltered
5. 5
   Otroevaporated solvent under vacuum
6. 6
   OtroPurified by column chromatography

Procedimiento

Allylbenzene (255 μL, 1.9 mmol), 4-bromobenzoic acid (523 mg, 2.6 mmol), Et3N (0.91 mL, 6.5 mmol), Palladium (II) Acetate (16 mg, 0.052 mmol), triphenylphosphine (60 mg, 0.21 mmol) and acetonitrile (5 mL) were stirred at reflux overnight in a round bottom flask. Added HCl 1N, extracted with EtOAc, dried the organic layer on anhydrous MgSO4, filtered, evaporated solvent under vacuum. Purified by column chromatography using 10% MeOH/CH2Cl2 yielded 90 mg (14%) of mixture of two regioisomers 54. The mixture was then submitted for hydrogenation without further characterization.

Fuente