Sodium Hydroxide → 3-(2-Bromo-5-(trifluoromethyl)phenyl)propanoic acid

HRID 2178766Notes

Reaction equation

HRID 2178766 reaction equation
C([O:3][C:4](=[O:23])[CH:5]([CH2:11][C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=1[Br:22])C(OCC)=O)C.[OH-].[Na+]>C(O)C.O>[Br:22][C:13]1[CH:14]=[CH:15][C:16]([C:18]([F:21])([F:20])[F:19])=[CH:17][C:12]=1[CH2:11][CH2:5][C:4]([OH:23])=[O:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53704455Diethyl [2-bromo-5-(trifluoromethyl)benzyl]malonate

Product 1

HCID 248204723-(2-Bromo-5-(trifluoromethyl)phenyl)propanoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of diethyl[2-bromo-5-(trifluoromethyl)benzyl]malonate (22.9 g, 57.6 mmol) in ethanol (100 mL) and water (50 mL) was added a 5 M solution of sodium hydroxide in water (30 mL). The mixture was heated to reflux for 2 h. Ethanol was removed by evaporation. The aqueous layer was extracted with ether and then acidified with concentrated HCl to pH 5 at which time a lot of white solid precipitated out. The solid was collected by filtration. The filtrate was extracted with ethyl acetate twice, and the extracts were washed with brine, dried (MgSO4) and concentrated to give a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 h
  3. customEthanol was removed by evaporation
  4. extractionThe aqueous layer was extracted with ether
  5. customprecipitated out
  6. filtrationThe solid was collected by filtration
  7. extractionThe filtrate was extracted with ethyl acetate twice
  8. washthe extracts were washed with brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated
  11. customto give a white solid

Sources & evidence

ORD record
ord-ec3dd48ea122423e8a753dc7138a3788
Source dataset
uspto-grants-2015_06
Patent number
US09067921B2

Reaction notes

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