反应 #2006420

ord-592c51d73cd445e9aa8e2c62c68ddc75

反应方程式

C=CCc1ccccc1
Allylbenzene
O=C(O)c1ccc(Br)cc1
4-bromobenzoic acid
CCN(CC)CC
Et3N
c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenylphosphine
O=C(O)c1ccc(C=CCc2ccccc2)cc1.O=C(O)c1ccc(CC=Cc2ccccc2)cc1
mixture
收率 19.9%
O=C(O)c1ccc(C=CCc2ccccc2)cc1.O=C(O)c1ccc(CC=Cc2ccccc2)cc1
4(3-Phenylpropenyl)-benzoic Acid 4-(3-Phenyl-2-propenyl)-benzoic Acid
收率 19.9%

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    温度at reflux overnight in a round bottom flask
  2. 2
    萃取Added HCl 1N, extracted with EtOAc
  3. 3
    干燥dried the organic layer on anhydrous MgSO4
  4. 4
    过滤filtered
  5. 5
    其他evaporated solvent under vacuum
  6. 6
    其他Purified by column chromatography

实验过程

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.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: USRE043343E1uspto-grants-2012_05