Oxalyl chloride → 2-Bromo-4-fluorobenzoyl chloride

HRID 1889011Notes

Reaction equation

HRID 1889011 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C(Cl)(=O)C([Cl:15])=O>ClCCl.CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([Cl:15])=[O:5]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 12681692-Bromo-4-fluorobenzoic acid

Product 1

HCID 27833462-Bromo-4-fluorobenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

2-Bromo-4-fluorobenzoic acid (1.533 g, 7 mmol, commercially available from e.g. Sigma-Aldrich, Apollo or Fluorochem) in dichloromethane (DCM) (40 mL) was cooled to 0° C., before oxalyl chloride (0.674 mL, 7.70 mmol) and a few drops of DMF (cat.) were added. The solution was then stirred under argon for 3 hours. The solvent was then evaporated in vacuo and the remaining residue was azeotroped with toluene (2×20 mL) to yield the product in 1.645 g.

Workup

  1. additionwere added
  2. customThe solvent was then evaporated in vacuo
  3. customthe remaining residue was azeotroped with toluene (2×20 mL)
  4. customto yield the product in 1.645 g

Sources & evidence

ORD record
ord-4254f079177f44c6944f9d2236a70f7c
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

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