Trifluoroacetic acid → 2-[(2,5-Dichloropyridin-3-yl)oxy]-2-methylpropionic acid

HRID 1026539Notes

Reaction equation

HRID 1026539 reaction equation
[Cl:1][C:2]1[C:7]([O:8][C:9]([CH3:18])([CH3:17])[C:10]([O:12]C(C)(C)C)=[O:11])=[CH:6][C:5]([Cl:19])=[CH:4][N:3]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[C:7]([O:8][C:9]([CH3:17])([CH3:18])[C:10]([OH:12])=[O:11])=[CH:6][C:5]([Cl:19])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86671386Tert-butyl 2-[(2,5-dichloropyridin-3-yl)oxy]-2-methylpropionate

Product 1

HCID 866713872-[(2,5-Dichloropyridin-3-yl)oxy]-2-methylpropionic acidYield 125.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane solution (157 ml) of tert-butyl 2-[(2,5-dichloropyridin-3-yl)oxy]-2-methylpropionate (79.1 g) was added at 0° C. trifluoroacetic acid (157 ml). The reaction solution was brought back to room temperature, stirred overnight, and then concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed sequentially with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was azeotroped with toluene to afford 2-[(2,5-dichloropyridin-3-yl)oxy]-2-methylpropionic acid (81.1 g).

Workup

  1. customwas brought back to room temperature
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed sequentially with water and saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was azeotroped with toluene

Sources & evidence

ORD record
ord-0b56ff09ed5144dda50816a792bad4d0
Source dataset
uspto-grants-2014_05
Patent number
US08729095B2

Reaction notes

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