Réaction #2006420

Équation de réaction

Allylbenzene

4-bromobenzoic acid

Et3N

triphenylphosphine

→

mixture

Rendement 19.9%

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

Rendement 19.9%

Solvants

acetonitrile

Conditions de réaction

Traitement

1. 1
   Températureat reflux overnight in a round bottom flask
2. 2
   ExtractionAdded HCl 1N, extracted with EtOAc
3. 3
   Séchagedried the organic layer on anhydrous MgSO4
4. 4
   Filtrationfiltered
5. 5
   Autreevaporated solvent under vacuum
6. 6
   AutrePurified by column chromatography

Mode opératoire

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.

Source