trans-3,5-Difluorocinnamic acid → 3-(3,5-Difluorophenyl)propionic acid

HRID 601706

Reaction equation

HRID 601706 reaction equation
[F:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]([OH:13])=[O:12])[CH:5]=[C:6]([F:8])[CH:7]=1>[Pd].C(OCC)(=O)C.C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 1

HCID 5374941trans-3,5-Difluorocinnamic acid

Product 1

HCID 36694983-(3,5-Difluorophenyl)propionic acidYield 99%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To palladium on activated charcoal (10 wt %, 2.5 g) was added a solution of (E)-3-(3,5-difluorophenyl)acrylic acid (25 g) in a mixture of ethyl acetate (100 mL) and ethyl alcohol (400 mL). The mixture was put on hydrogenator on 50 psi for 6 h. The catalyst was filtered and the solvent was removed to give 25.0 g the title compound (99% yield): 1H NMR (CDCl3, 500 MHz) δ 2.67 (2H, t, J=10 Hz), 2.93 (2H, t, J=10 Hz), 6.65 (1H, m), 6.72 (2H, m).

Workup

  1. filtrationThe catalyst was filtered
  2. customthe solvent was removed

Sources & evidence

ORD record
ord-9bcada9b9e39424d88d9fb37f030a313
Source dataset
uspto-grants-2011_03
Patent number
US07902218B2

Linked notes

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