Reaction #2006420

Reaction equation

Allylbenzene

4-bromobenzoic acid

Et3N

triphenylphosphine

→

mixture

Yield 19.9%

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

Yield 19.9%

Solvents

acetonitrile

Conditions

Workup

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

Procedure

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