Hydrochloric Acid → 1-(4-Bromo-3-fluorophenyl)cyclopropane-1-carboxylic acid

HRID 1879434Notes

Reaction equation

HRID 1879434 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]#N)[CH2:10][CH2:9]2)=[CH:4][C:3]=1[F:13].[OH-:14].[Na+].[OH:16]O.Cl>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([OH:16])=[O:14])[CH2:10][CH2:9]2)=[CH:4][C:3]=1[F:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 117156671-(4-Bromo-3-fluorophenyl)cyclopropane-1-carbonitrile

Product 1

HCID 116518041-(4-Bromo-3-fluorophenyl)cyclopropane-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 4-bromo-3-fluorophenylcyclopropanenitrile (21 mmoles) in methanol (10 ml) is added with a 35% NaOH aqueous solution (40 ml) and a 35% H2O2 aqueous solution (3 ml), then is refluxed for 4 hours, cooled at room temperature and added with 2N HCl (250 ml). The precipitated solid is collected by filtration and redissolved in a 5% NaHCO3 aqueous solution (300 ml). The insoluble fraction is filtered off and the clear filtrate is acidified to pH=2 with 2N HCl. The product precipitates as a white solid, which is recovered by filtration and dried under vacuum.

Workup

  1. filtrationThe precipitated solid is collected by filtration
  2. dissolutionredissolved in a 5% NaHCO3 aqueous solution (300 ml)
  3. filtrationThe insoluble fraction is filtered off
  4. customThe product precipitates as a white solid, which
  5. filtrationis recovered by filtration
  6. customdried under vacuum

Sources & evidence

ORD record
ord-14e130393cf9446890e213a6949b9607
Source dataset
uspto-grants-2012_11
Patent number
US08314268B2

Reaction notes

Loading…