Potassium Hydroxide → 1-[(4-Fluorophenyl)carbamoyl]cyclopropanecarboxylic Acid

HRID 1517899Notes

Reaction equation

HRID 1517899 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2([C:14]([O:16]CC)=[O:15])[CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1.[OH-].[K+]>CCO.C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2([C:14]([OH:16])=[O:15])[CH2:12][CH2:13]2)=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 56956060Ethyl 1-((4-fluorophenyl)carbamoyl)cyclopropane-1-carboxylate

Product 1

HCID 210815301-[(4-Fluorophenyl)carbamoyl]cyclopropanecarboxylic AcidYield 97%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a mixture of ethyl 1-((4-fluorophenyl)carbamoyl)cyclopropane-carboxylate (8.9 g, 35.4 mmol) in EtOH/THF (50/50 mL, Guangdong Guanghua Chem. Co. Ltd.) was added KOH (3.98 g, 70.8 mmol, Guangdong Guanghua Chem. Co. Ltd.) aqueous solution dropwise via a syringe. The reaction was stirred at RT overnight under N2. The mixture was concentrated in vacuo. The residue was then acidified to pH 2 with 5 N HCl and extracted with EtOAc (150 mL×4), the combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was recrystallized in EtOAc/n-hexane (1:40 v/v) to give the title compound as a white solid (7.66 g, 97%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. extractionextracted with EtOAc (150 mL×4)
  3. dry with materialthe combined organic phases were dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was recrystallized in EtOAc/n-hexane (1:40 v/v)

Sources & evidence

ORD record
ord-ac2c9f5e83364e0e87f9feddae4458ce
Source dataset
uspto-grants-2012_07
Patent number
US08232294B2

Reaction notes

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