Hydrochloric Acid → 2,2-Difluoro-2-phenylacetic acid

HRID 1060209Notes

Reaction equation

HRID 1060209 reaction equation
[F:1][C:2]([F:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([O:5]CC)=[O:4].[OH-].[Na+].Cl>>[C:8]1([C:2]([C:3]([OH:5])=[O:4])([F:14])[F:1])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10631860Ethyl 2,2-difluoro-2-phenylacetate

Product 1

HCID 7261532,2-Difluoro-2-phenylacetic acidYield 81%

Procedure

A suspension of ethyl 2,2-difluoro-2-phenylacetate (6.0 g, 30 mmol), as prepared in the preceding step, in 1 N NaOH (36 mL, 36 mmol) was stirred at ambient temperature. After 36 hours, the reaction became almost homogeneous. The mixture was acidified with 1N HCl (36 mL), and extracted with DCM twice. The extracts were combined, washed with H2O, dried over Na2SO4, and concentrated to give the title compound (3.85 g, 81% yield) as a pale yellow solid, that was used without further purification.

Workup

  1. extractionextracted with DCM twice
  2. washwashed with H2O
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7d4f32328f614796a2679ebe6768c7de
Source dataset
uspto-grants-2003_02
Patent number
US06521663B2

Reaction notes

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