Methanol → Methyl 4-fluoro-2-(trifluoromethyl)benzoate

HRID 1978180Notes

Reaction equation

HRID 1978180 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.[C:15](Cl)(=O)C(Cl)=O.CO>ClCCl.CN(C)C=O>[CH3:15][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([F:1])=[CH:3][C:4]=1[C:11]([F:12])([F:13])[F:14]

Participants

6

Reactant 3

HCID 887MethanolHCID 65578Oxalyl chlorideHCID 6882554-Fluoro-2-(trifluoromethyl)benzoic acid

Product 1

HCID 15541084Methyl 4-fluoro-2-(trifluoromethyl)benzoateYield 65.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of 4-fluoro-2-trifluoromethylbenzoic acid (25.6 g, 123.0 mmol) in dichloromethane (250 mL) containing a few drops of dimethylformamide was treated dropwise under nitrogen with oxalyl chloride (11.3 mL, 129.5 mmol). After the gas evolution subsided, the reaction mixture was refluxed for an additional 15 minutes. The mixture was cooled and methanol (50 mL) was added. After stirring for 2 hrs, the reaction was concentrated, and the residue was partitioned between dichloromethane and water. The organic phase was washed with saturated aqueous sodium bicarbonate, dried over sodium sulfate, and evaporated to dryness to give 18.0 g of the title compound as a golden oil.

Workup

  1. temperaturethe reaction mixture was refluxed for an additional 15 minutes
  2. temperatureThe mixture was cooled
  3. concentrationthe reaction was concentrated
  4. customthe residue was partitioned between dichloromethane and water
  5. washThe organic phase was washed with saturated aqueous sodium bicarbonate
  6. dry with materialdried over sodium sulfate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-e744e9f1d82f44e5810acc720d908e54
Source dataset
uspto-grants-2001_05
Patent number
US06235900B1

Reaction notes

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