Reaction #41968

Reaction equation

3,5-difluorocinnamic acid

sulfuric acid

→

title compound

Yield 92.2%

3-(3,5-difluoro-phenyl)-propionic acid

Yield 92.2%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   FiltrationAfter filtering the catalyst
2. 2
   workup.ADDITIONdilute with ether
3. 3
   Washwash with water twice
4. 4
   Dryingdry over anhydrous sodium sulfate
5. 5
   Concentrationconcentrate

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).

Source