Trifluoroacetic acid → 4-Cyano-2-(trifluoromethyl)benzoic acid

HRID 389087Notes

Reaction equation

HRID 389087 reaction equation
FC(F)(F)C(O)=O.[C:8]([C:10]1[CH:22]=[CH:21][C:13]([C:14]([O:16]C(C)(C)C)=[O:15])=[C:12]([C:23]([F:26])([F:25])[F:24])[CH:11]=1)#[N:9]>ClCCl>[C:8]([C:10]1[CH:22]=[CH:21][C:13]([C:14]([OH:16])=[O:15])=[C:12]([C:23]([F:24])([F:25])[F:26])[CH:11]=1)#[N:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58244301HCID 58244301, compound

Product 1

HCID 534150224-Cyano-2-(trifluoromethyl)benzoic acidYield 88.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.55 ml) was added to a solution of tert-butyl 4-cyano-2-(trifluoromethyl)benzoate (194 mg) in dichloromethane (2 ml) under ice cooling, followed by stirring at the temperature for one hour. It was warmed to room temperature and stirred for 17 hours. The reaction solution was concentrated under reduced pressure, a 1M aqueous sodium hydroxide solution (2 ml) was added thereto, followed by washing with diethyl ether. 1M hydrochloric acid (2 ml) was added to the aqueous layer, followed by extraction with ethyl acetate-methanol mixed solution (4:1). The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain 4-cyano-2-(trifluoromethyl)benzoic acid (136 mg) as a colorless solid.

Workup

  1. stirringstirred for 17 hours
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additiona 1M aqueous sodium hydroxide solution (2 ml) was added
  4. washby washing with diethyl ether
  5. addition1M hydrochloric acid (2 ml) was added to the aqueous layer
  6. extractionfollowed by extraction with ethyl acetate-methanol mixed solution (4:1)
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-98c10f0230714643bd4fbbc1f9fe6030
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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