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Water → 2-(4-Bromo-2-chlorophenyl)acetic acid

HRID 1641533
Notes
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Reaction equation

HRID 1641533 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#N)=[C:4]([Cl:11])[CH:3]=1.[OH2:12].[OH-:13].[K+]>C(O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]([OH:13])=[O:12])=[C:4]([Cl:11])[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 58762522(4-Bromo-2-chlorophenyl)acetonitrile

Product 1

HCID 534036172-(4-Bromo-2-chlorophenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To 4-bromo-2-chlorobenzyl cyanide (383 g) of Reference Example 14 were added water (908 mL), ethanol (6812 mL) and 85% aqueous potassium hydroxide solution (549 g), and the mixture was stirred at an inside temperature of 75° C. for 13 hr. The mixture was concentrated, and diisopropyl ether (4500 mL) and water were added. The aqueous layer was neutralized with 1M hydrochloric acid, and partitioned and extracted with ethyl acetate. The organic layer was washed with 25% brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residual crude crystals were recrystallized from a mixed solvent of diisopropyl ether and hexane to give the title compound (240 g) as pale-yellow crystals.

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiisopropyl ether (4500 mL) and water were added
  3. custompartitioned
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with 25% brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residual crude crystals were recrystallized from a mixed solvent of diisopropyl ether and hexane

Sources & evidence

ORD record
ord-f69d2b54a0f14b17b43820f2d9b160a4
Source dataset
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08114902B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes