Water → 2-(2,5-Difluorophenyl)cyclopropane-1-carboxylic acid

HRID 857018Notes

Reaction equation

HRID 857018 reaction equation
CON(C)[C:4]([CH:6]1[CH2:8][CH:7]1[C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[F:16])=[O:5].[OH2:18].[OH-].[Na+]>CO>[F:16][C:10]1[CH:11]=[CH:12][C:13]([F:15])=[CH:14][C:9]=1[CH:7]1[CH2:8][CH:6]1[C:4]([OH:18])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 587594682-(2,5Difluoro-phenyl)-cyclopropanecarboxylic acid methoxy-methyl-amide

Product 1

HCID 218646562-(2,5-Difluorophenyl)cyclopropane-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(2,5-difluoro-phenyl)-cyclopropanecarboxylic acid methoxy-methyl-amide (9.6 g), water (20 mL), and NaOH (3.2 g) in MeOH (40 mL) was refluxed for 3 h. The reaction mixture was cooled down to room temperature and concentrated in vacuo. The residue was acidified by 6 N HCl followed by extraction with CH2Cl2. The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo to give the title compound (7.8 g).

Workup

  1. temperaturewas refluxed for 3 h
  2. concentrationconcentrated in vacuo
  3. extractionfollowed by extraction with CH2Cl2
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6641a8c6dfa44a82a822587065683740
Source dataset
uspto-grants-2006_12
Patent number
US07144881B2

Reaction notes

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