Acetyl chloride → Methyl 2-chloro-4,5-difluorobenzoate

HRID 1041883Notes

Reaction equation

HRID 1041883 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:13](Cl)(=O)C>CO>[CH3:13][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([F:12])[C:9]([F:11])=[CH:10][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 7371712-Chloro-4,5-difluorobenzoic acid

Product 1

HCID 22149760Methyl 2-chloro-4,5-difluorobenzoateYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred suspension of 5.0 g (26 mmol) 2-Chloro-4,5-difluoro-benzoic acid (Apollo) and 50 ml methanol were added 7.41 ml (104 mmol) acetyl chloride drop wisely at 0° C. The reaction mixture was stirred over night, filtered and concentrated. The residue was diluted with dichloromethane, washed with diluted sodium hydrogen carbonate solution, dried with sodium sulphate and concentrated. The residue was purified by column chromatography (hexane:ethylacetate). The desired product 22a was obtained in 84% yield (4.51 g, 21.8 mmol).

Workup

  1. customdrop wisely at 0° C
  2. filtrationfiltered
  3. concentrationconcentrated
  4. additionThe residue was diluted with dichloromethane
  5. washwashed with diluted sodium hydrogen carbonate solution
  6. dry with materialdried with sodium sulphate
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (hexane:ethylacetate)

Sources & evidence

ORD record
ord-d8190e6abcb7421199a5d4e7f0654226
Source dataset
uspto-grants-2013_10
Patent number
US08557776B2

Reaction notes

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