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

HRID 430590Notes

Reaction equation

HRID 430590 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-benzoyl fluoride are added dropwise to 1460 ml of methanol and 340 g of triethylamin, while cooling with ice. The mixture is stirred at room temperature for 1 hour. The reaction mixture is concentrated in vacuo and the resulting residue is taken up in water and methylene chloride. The water is extracted with methylene chloride once more. The organic phase is dried with Na2CO3 and concentrated in vacuo. The resulting residue is distilled in vacuo.

Workup

  1. temperaturewhile cooling with ice
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. extractionThe water is extracted with methylene chloride once more
  4. dry with materialThe organic phase is dried with Na2CO3
  5. concentrationconcentrated in vacuo
  6. distillationThe resulting residue is distilled in vacuo

Sources & evidence

ORD record
ord-105e54b9e56840beb2bb29144385b04e
Source dataset
uspto-grants-2001_11
Patent number
US06323213B1

Reaction notes

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