Oxalyl chloride → HCID 59347787, compound

HRID 20827Notes

Reaction equation

HRID 20827 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]([C:15]([F:18])([F:17])[F:16])[C:3]=1[C:4](O)=[O:5].C(Cl)(=O)C([Cl:22])=O>C(Cl)Cl.CN(C=O)C>[CH3:1][C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]([C:15]([F:18])([F:17])[F:16])[C:3]=1[C:4]([Cl:22])=[O:5]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 593477712-Methyl-4,6-bis(trifluoromethyl)benzoic acid

Product 1

HCID 59347787HCID 59347787, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-methyl-4,6-bis(trifluoromethyl)benzoic acid D52 alternative method (400 mg, approximately 1.47 mmol) in DCM (5 ml), containing DMF (1 drop), was treated with oxalyl chloride (166 ul, 1.91 mmol) and stirred under argon for 1 hour. The solvent was carefully removed under reduced pressure and the residue re-evaporated from further DCM. The mixture of acid chlorides was then treated with methanol (3 ml) and kept at room temperature for 2 hours after which time the solvent was again carefully removed under reduced pressure. NMR data indicated this to be a mixture of the title product 2-methyl-4,6-bis(trifluoromethyl)benzoyl chloride and methyl 2,4-bis(trifluoromethyl)benzoate. The mixture was used without further purification.

Workup

  1. customThe solvent was carefully removed under reduced pressure
  2. customthe residue re-evaporated from further DCM
  3. additionThe mixture of acid chlorides
  4. additionwas then treated with methanol (3 ml)
  5. waitkept at room temperature for 2 hours
  6. customafter which time the solvent was again carefully removed under reduced pressure
  7. additiona mixture of the title product 2-methyl-4,6-bis(trifluoromethyl)benzoyl chloride and methyl 2,4-bis(trifluoromethyl)benzoate
  8. customThe mixture was used without further purification

Sources & evidence

ORD record
ord-946a3dfc5a724e79bf84f72c6a470866
Source dataset
uspto-grants-2010_06
Patent number
US07745642B2

Reaction notes

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