Trifluoroacetic acid → 3-(5-Methylpyridin-2-yl)-5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzoic acid

HRID 888374Notes

Reaction equation

HRID 888374 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH:18]=[C:19]([C:21]([OH:30])([C:26]([F:29])([F:28])[F:27])[C:22]([F:25])([F:24])[F:23])[CH:20]=2)[C:11]([O:13]C(C)(C)C)=[O:12])=[N:6][CH:7]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH:18]=[C:19]([C:21]([OH:30])([C:22]([F:25])([F:23])[F:24])[C:26]([F:27])([F:28])[F:29])[CH:20]=2)[C:11]([OH:13])=[O:12])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86646754Tert-butyl 3-(5-methylpyridin-2-yl)-5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzoate

Product 1

HCID 866467553-(5-Methylpyridin-2-yl)-5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. DCM (6.8 mL) solution of tert-butyl 3-(5-methylpyridin-2-yl)-5-[92,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzoate (0.6 g, 1.38 mmol) from step C was added trifluoroacetic acid (6.9 mL). The mixture was warmed to rt over 2 h and concentrated to dryness to give a gummy solid. The crude title compound was used in step E without further purification. LC-MS (M+H)=380.1

Workup

  1. customTo a 0° C
  2. concentrationconcentrated to dryness
  3. customto give a gummy solid
  4. customThe crude title compound was used in step E without further purification

Sources & evidence

ORD record
ord-cbdc4f47781346e296927b038ed1f029
Source dataset
uspto-grants-2012_08
Patent number
US08247401B2

Reaction notes

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