Oxalyl chloride → 3-Chloro-4-fluoro-2-methylbenzoyl chloride

HRID 1889009Notes

Reaction equation

HRID 1889009 reaction equation
[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5](O)=[O:6].C(Cl)(=O)C([Cl:16])=O>ClCCl.CN(C=O)C>[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([Cl:16])=[O:6]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 665993413-Chloro-4-fluoro-2-methylbenzoic acid

Product 1

HCID 866667393-Chloro-4-fluoro-2-methylbenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

3-chloro-4-fluoro-2-methylbenzoic acid (I57)(0.754 g, 4 mmol) in dichloromethane (DCM) (30 mL) was cooled to 0° C., before oxalyl chloride (0.385 mL, 4.40 mmol) and a few drops of DMF (cat.) were added. The solution was then stirred under argon for 3 hours, before the solvent was evaporated in vacuo. The remaining residue was then azeotroped with toluene to yield the product in 0.819 g.

Workup

  1. additionwere added
  2. customwas evaporated in vacuo
  3. customThe remaining residue was then azeotroped with toluene
  4. customto yield the product in 0.819 g

Sources & evidence

ORD record
ord-d80a06581fdb4d54b9d00c6a1995f8c0
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

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