Methanol → Methyl 3-bromo-2,4,5-trifluorobenzoate

HRID 367012Notes

Reaction equation

HRID 367012 reaction equation
[Br:1][C:2]1[C:3]([F:13])=[C:4]([CH:8]=[C:9]([F:12])[C:10]=1[F:11])[C:5](F)=[O:6].[CH3:14][OH:15]>C(N(CC)CC)C>[Br:1][C:2]1[C:3]([F:13])=[C:4]([CH:8]=[C:9]([F:12])[C:10]=1[F:11])[C:5]([O:15][CH3:14])=[O:6]

Participants

4

Reactant 2

HCID 887MethanolHCID 141498723-Bromo-2,4,5-trifluorobenzoyl fluoride

Product 1

HCID 18459836Methyl 3-bromo-2,4,5-trifluorobenzoate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

772 g of 3-bromo-2,4,5-trifluoro-benzoylfluoride are added dropwise with ice-cooling to a mixture of 1460 ml of methanol and 340 g of triethylamine. Stirring is carried out at room temperature for 1 hour. The reaction mixture is concentrated, the residue is taken up in water and methylene chloride, and the aqueous phase is again extracted by shaking with methylene chloride. After drying the organic phase over sodium sulphate, it is concentrated and the residue is distilled in vacuo. 752.4 g of methyl 3-bromo-2,4,5-trifluoro-benzoate of boiling point 122° C./20 mbar are obtained.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. extractionmethylene chloride, and the aqueous phase is again extracted
  3. stirringby shaking with methylene chloride
  4. dry with materialAfter drying the organic phase over sodium sulphate, it
  5. concentrationis concentrated
  6. distillationthe residue is distilled in vacuo

Sources & evidence

ORD record
ord-9bb366711f7b4f87b41193cf93bbfc82
Source dataset
uspto-grants-2000_10
Patent number
US06133260

Reaction notes

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