Sulfuric Acid → 3-(3,5-Difluorophenyl)propionic acid

HRID 13690

Reaction equation

HRID 13690 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([F:13])[CH:12]=1)[CH:5]=[CH:6][C:7]([OH:9])=[O:8].S(=O)(=O)(O)O>[Pd].O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([CH2:5][CH2:6][C:7]([OH:9])=[O:8])[CH:10]=[C:11]([F:13])[CH:12]=1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 5228103-(3,5-Difluorophenyl)acrylic acid

Product 1

HCID 36694983-(3,5-Difluorophenyl)propionic acidYield 92.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Hydrogenate a mixture of 3,5-difluorocinnamic acid (10.0 g, 54.3 mmol), 5% palladium on carbon (1.5 g), and concentrated sulfuric acid (10 ml) in tetrahydrofuran (195 ml) at 60 psi at room temperature overnight. After filtering the catalyst, dilute with ether, wash with water twice, dry over anhydrous sodium sulfate, and concentrate to obtain the title compound as clear colorless crystals (9.32 g, 92%). NMR (400 MHz, CDCl3): δ 2.67 (t, 2H), 2.94 (t, 2H), 6.65 (t, 1H), 6.74 (d, 2H).

Workup

  1. filtrationAfter filtering the catalyst
  2. additiondilute with ether
  3. washwash with water twice
  4. dry with materialdry over anhydrous sodium sulfate
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-53d1feeb0cf9479f8fdc097813fafe67
Source dataset
uspto-grants-2010_06
Patent number
US07728150B2

Linked notes

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