Oxalyl chloride → 4-Chloro-2-methylbenzoyl chloride

HRID 1889006Notes

Reaction equation

HRID 1889006 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([CH3:11])[CH:3]=1.C(Cl)(=O)C([Cl:15])=O>ClCCl.CN(C=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:15])=[O:7])=[C:4]([CH3:11])[CH:3]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 3482694-Chloro-2-methylbenzoic acid

Product 1

HCID 128464844-Chloro-2-methylbenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

4-Chloro-2-methylbenzoic acid (1.365 g, 8 mmol, commercially available from e.g. Maybridge, Fluorochem or Sigma-Aldrich) in dichloromethane (DCM) (40 mL) was cooled to 0° C., before oxalyl chloride (0.770 mL, 8.80 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 1.464 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 1.464 g

Sources & evidence

ORD record
ord-d9408511425d4520a1dd4af23444c46a
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

Loading…