Oxalyl chloride → 4-methyl-2-(trifluoromethyl)benzoyl Chloride

HRID 1889013Notes

Reaction equation

HRID 1889013 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.C(Cl)(=O)C([Cl:18])=O>ClCCl.CN(C=O)C>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:18])=[O:7])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 27755914-methyl-2-(trifluoromethyl)benzoic Acid

Product 1

HCID 27756064-methyl-2-(trifluoromethyl)benzoyl Chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

4-Methyl-2-(trifluoromethyl)benzoic acid (1 g, 4.90 mmol, commercially available from e.g. Fluorochem or ABCR) in dichloromethane (DCM) (40 mL) was cooled to 0° C., before oxalyl chloride (0.472 mL, 5.39 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 1.051 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 1.051 g

Sources & evidence

ORD record
ord-ea54ac9061914b51a111430474434620
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

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