Water → HCID 68804800, compound

HRID 1270779Notes

Reaction equation

HRID 1270779 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:10][CH2:9]2)=[CH:4][C:3]=1[CH2:11][C:12]#N.[OH-:14].[Na+].[OH2:16]>CCO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:10][CH2:9]2)=[CH:4][C:3]=1[CH2:11][C:12]([OH:16])=[O:14]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 68804489HCID 68804489, compound

Product 1

HCID 68804800HCID 68804800, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the above nitrile (12 g) in EtOH (400 mL), is added NaOH (36.6 g) and water (200 mL). The reaction is refluxed for 2 hours and cooled to room temperature. After the ethanol is removed under reduced pressure, the residue is cooled to 0° C. and acidified to pH 1–2 with 3 N HCl. The phenylacetic acid is extracted into ethyl acetate and the aqueous layer discarded. The organic phase is washed with brine, dried (Na2SO4) and concentrated in vacuo to afford 2-bromo-5-cyclopropylphenylacetic acid.

Workup

  1. temperatureThe reaction is refluxed for 2 hours
  2. customAfter the ethanol is removed under reduced pressure
  3. temperaturethe residue is cooled to 0° C.
  4. extractionThe phenylacetic acid is extracted into ethyl acetate
  5. washThe organic phase is washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ecaf10a505b542e187abff20f6ea1036
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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