Acetyl chloride → Methyl 2-(3,5-difluorophenyl)acetate

HRID 133178Notes

Reaction equation

HRID 133178 reaction equation
[C:1](Cl)(=O)C.[F:5][C:6]1[CH:7]=[C:8]([CH2:13][C:14]([OH:16])=[O:15])[CH:9]=[C:10]([F:12])[CH:11]=1>CO>[F:5][C:6]1[CH:7]=[C:8]([CH2:13][C:14]([O:16][CH3:1])=[O:15])[CH:9]=[C:10]([F:12])[CH:11]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 1454243,5-Difluorophenylacetic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution comprising 25 ml of acetyl chloride in 250 ml of methanol is prepared at 0° C., then, at ambient temperature, 25.5 g of 3,5-difluorophenylacetic acid are dissolved in this solution and the solution is left stirring at AT. The reaction is monitored by thin layer chromatography. After the starting material has disappeared, the medium is evaporated under reduced pressure and then the residue is dissolved in 250 ml of MTBE. The organic phase is washed three times with 100 ml of water, dried over MgSO4 and then evaporated to dryness under reduced pressure. 26.9 g of the expected compound are obtained.

Workup

  1. customis prepared at 0° C.
  2. waitthe solution is left
  3. customthe medium is evaporated under reduced pressure
  4. dissolutionthe residue is dissolved in 250 ml of MTBE
  5. washThe organic phase is washed three times with 100 ml of water
  6. dry with materialdried over MgSO4
  7. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-acf6b46217f344d49eea2f2e377ddc40
Source dataset
uspto-grants-2008_06
Patent number
US07390818B2

Reaction notes

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