(E)-4-(4-bromo-2-fluorophenyl)but-3-enoic acid → 4-(4-Bromo-2-fluorophenyl)butanoic acid

HRID 2089480Notes

Reaction equation

HRID 2089480 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[CH2:10][C:11]([OH:13])=[O:12])=[C:4]([F:14])[CH:3]=1>C(OCC)(=O)C.[Pd]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[C:4]([F:14])[CH:3]=1

Participants

4

Reactant 1

HCID 67547376(E)-4-(4-bromo-2-fluorophenyl)but-3-enoic acid

Product 1

HCID 606766074-(4-Bromo-2-fluorophenyl)butanoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (E)-4-(4-bromo-2-fluoro-phenyl)-but-3-enoic acid (0.730 g, 2.536 mmol) in ethyl acetate (12 mL) is added palladium on carbon (10% wt., 0.270 g, 0.254 mmol) and the flask is flushed with hydrogen. After 16 hours under a H2 atmosphere (balloon pressure), the mixture is filtered, concentrated and then resubmitted to the same conditions. After 6 hours, the mixture is filtered and concentrated to give 4-(4-bromo-2-fluoro-phenyl)-butyric acid, which is used in the next step without purification.

Workup

  1. customthe flask is flushed with hydrogen
  2. filtrationthe mixture is filtered
  3. concentrationconcentrated
  4. waitAfter 6 hours
  5. filtrationthe mixture is filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3c38211921b74f8bbe26a5585b3c3c4b
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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