Hydrochloric Acid → 2,2-Difluoro-2-(5-fluoropyridin-2-yl)acetic acid

HRID 473179Notes

Reaction equation

HRID 473179 reaction equation
[F:1][C:2]([F:13])([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][N:7]=1)[C:3]([O-:5])=[O:4].[Na+].Cl>CCOC(C)=O>[F:13][C:2]([F:1])([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][N:7]=1)[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66609989Sodium 2,2-difluoro-2-(5-fluoropyridin-2-yl)acetate

Product 1

HCID 666095532,2-Difluoro-2-(5-fluoropyridin-2-yl)acetic acidYield 95.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To sodium 2,2-difluoro-2-(5-fluoropyridin-2-yl)acetate from Example 2 step B (1 g, 4.69 mmol) were added EtOAc (50 mL) and 4 N HCl (50 mL) and the mixture was shaken. The organic phase was separated, dried over sodium sulfate, and concentrated under reduced pressure to afford 2,2-difluoro-2-(5-fluoropyridin-2-yl)acetic acid (852 mg, 95%) as an oil that solidified upon standing. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.88-8.03 (m, 3H).

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-622dcd9603414782be4756c5d3dc70e3
Source dataset
uspto-grants-2014_01
Patent number
US08633207B2

Reaction notes

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