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

HRID 2246771Notes

Reaction equation

HRID 2246771 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+].Cl.C([OH:19])C>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([OH:19])=[O:14])[CH2:10][CH2:9]2)=[CH:4][C:3]=1[F:13]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 117156671-(4-Bromo-3-fluorophenyl)cyclopropane-1-carbonitrile

Product 1

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

Conditions

Temperature
100 °C

Procedure

To a room temperature solution of 1-(4-bromo-3-fluorophenyl)cyclopropanecarbonitrile from Step 4 (4.3 g) in ethyl alcohol (40 mL) was added a solution of 20 mL of sodium hydroxide (25% NaOH in water W/W). The mixture was heated at 100° C. overnight. It was cooled to room temperature and poured into ice and hydrogen chloride (1 N), and extracted with dichloromethane (2×100 mL). The combined extracts were washed with brine, dried with magnesium sulfate and the solvent removed in vacuo. The residue was purified by swish using methyl t-butyl ether and hexanes to yield the title compound.

Workup

  1. temperatureIt was cooled to room temperature
  2. extractionextracted with dichloromethane (2×100 mL)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried with magnesium sulfate
  5. customthe solvent removed in vacuo
  6. customThe residue was purified

Sources & evidence

ORD record
ord-ddd4fc47883748bb8c21662a6040787f
Source dataset
uspto-grants-2010_03
Patent number
US07687524B2

Reaction notes

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