Reaktion #2006420

Reaktionsgleichung

Allylbenzene

4-bromobenzoic acid

Et3N

triphenylphosphine

→

mixture

Ausbeute 19.9%

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

Ausbeute 19.9%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux overnight in a round bottom flask
2. 2
   ExtraktionAdded HCl 1N, extracted with EtOAc
3. 3
   Trocknendried the organic layer on anhydrous MgSO4
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated solvent under vacuum
6. 6
   SonstigePurified by column chromatography

Vorschrift

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.

Quelle