Methyl 3-(3,5-difluorophenoxy)acrylate → Methyl 3-(3,5-difluorophenoxy)propanoate

HRID 2239300Notes

Reaction equation

HRID 2239300 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([F:15])[CH:14]=1)[O:5][CH:6]=[CH:7][C:8]([O:10][CH3:11])=[O:9]>[Pd].CO>[F:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([F:15])[CH:14]=1)[O:5][CH2:6][CH2:7][C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 1

HCID 68574715Methyl 3-(3,5-difluorophenoxy)acrylate

Product 1

HCID 62784269Methyl 3-(3,5-difluorophenoxy)propanoateYield 100.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl 3-(3,5-difluorophenoxy)acrylate (60.0 g, 280 mmol, STEP 5), and 10% palladium on carbon (1.0 g) in methanol (300 mL) was stirred under hydrogen gas (1 atmosphere) at room temperature for 18 hours. The reaction mixture was filtered through a pad of Celite, and washed with toluene (100 mL). The filtrate was concentrated in vacuum to afford the title compound (61.0 g, quant) as a colorless oil, which was used in the next step without further purification.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. washwashed with toluene (100 mL)
  3. concentrationThe filtrate was concentrated in vacuum

Sources & evidence

ORD record
ord-c38d876ad5194706b72bb68d71fdaec2
Source dataset
uspto-grants-2010_05
Patent number
US07723321B2

Reaction notes

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