Trifluoroacetic acid → 4-((5,6-Dichloropyridin-3-yl)methoxy)-2,5-difluorobenzoic acid

HRID 1525661Notes

Reaction equation

HRID 1525661 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][O:10][C:11]2[C:23]([F:24])=[CH:22][C:14]([C:15]([O:17]C(C)(C)C)=[O:16])=[C:13]([F:25])[CH:12]=2)[CH:5]=[N:6][C:7]=1[Cl:8].FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][O:10][C:11]2[C:23]([F:24])=[CH:22][C:14]([C:15]([OH:17])=[O:16])=[C:13]([F:25])[CH:12]=2)[CH:5]=[N:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86682568tert-Butyl 4-((5,6-dichloropyridin-3-yl)methoxy)-2,5-difluorobenzoate

Product 1

HCID 866825694-((5,6-Dichloropyridin-3-yl)methoxy)-2,5-difluorobenzoic acidYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-((5,6-dichloropyridin-3-yl)methoxy)-2,5-difluorobenzoate (Preparation 7, 0.49 g, 1.26 mmol) in dichloromethane (10 mL) was added trifluoroacetic acid (5 mL). The reaction mixture was stirred 18 hours at room temperature and the reaction mixture was concentrated in vacuo. The crude material was purified by preparative reverse phase column chromatography to afford the title compound as a white solid (210 mg, 50%).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe crude material was purified by preparative reverse phase column chromatography

Sources & evidence

ORD record
ord-4ec4741054a4499492203b1b3e663f06
Source dataset
uspto-grants-2015_07
Patent number
US09085517B2

Reaction notes

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