Ethyl 4-chlorocinnamate → Ethyl 3-(4-chlorophenyl)propanoate

HRID 1993908Notes

Reaction equation

HRID 1993908 reaction equation
[CH2:1]([O:3][C:4](=[O:14])/[CH:5]=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)[CH3:2].[H][H]>C(OCC)(=O)C.[Pd].[Br-].[Zn+2].[Br-]>[CH2:1]([O:3][C:4](=[O:14])[CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([Cl:13])=[CH:11][CH:12]=1)[CH3:2]

Participants

6

Reactant 2

HCID 5373977Ethyl 4-chlorocinnamateHCID 178418361HCID 178418361, compound

Product 1

HCID 10921830Ethyl 3-(4-chlorophenyl)propanoate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 10421208Zinc bromideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (E)-3-(4-chloro-phenyl)-acrylic acid ethyl ester (0.37 g, 1.73 mmol) in ethyl acetate (10 ml) were added palladium on activated charcoal (18 mg) and zinc bromide (80 mg, 0.35 mmol). The reaction vessel was then pressurized with hydrogen gas to a pressure of 1 atmosphere and the mixture was stirred for 18 h. The catalyst was then removed by filtration, washing with ethyl acetate, and the filtrate was concentrated in vacuo to yield a colourless oil which was used for the next step without further purification; MS (ISP): 214.2, 212.1 ([M+H]+.).

Workup

  1. customThe catalyst was then removed by filtration
  2. washwashing with ethyl acetate
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto yield a colourless oil which
  5. customwas used for the next step without further purification

Sources & evidence

ORD record
ord-f1131b1862374857aa7bbd6cbf0bacb1
Source dataset
uspto-grants-2010_01
Patent number
US07652055B2

Reaction notes

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