Hydrochloric Acid → Methyl 2-(3,5-difluorophenyl)acetate

HRID 602968Notes

Reaction equation

HRID 602968 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1.Cl.O1CCOC[CH2:15]1>CO>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH3:15])=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 1454243,5-Difluorophenylacetic acid

Product 1

HCID 22270748Methyl 2-(3,5-difluorophenyl)acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5.0 g (29.1 mmol) of 3,5-difluorophenylacetic acid and a solution of 20 mL (80 mmol) of HCl in dioxane (4M) in 60 mL CH3OH was heated at reflux for 6 h. After cooling, the solution was concentrated and the residue poured into 200 mL of ether/ethyl acetate (1/1). The organic layer was washed with 20 mL of water, dried over Na2SO4 and concentrated to afford the title compound.

Workup

  1. temperatureat reflux for 6 h
  2. temperatureAfter cooling
  3. concentrationthe solution was concentrated
  4. additionthe residue poured into 200 mL of ether/ethyl acetate (1/1)
  5. washThe organic layer was washed with 20 mL of water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-974832bc99994fad91ad4c782978c590
Source dataset
uspto-grants-2011_03
Patent number
US07906652B2

Reaction notes

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