Hydrogen Bromide → 2-[3-Hydroxy-5-(trifluoromethyl)phenyl]propanoic acid

HRID 1686424Notes

Reaction equation

HRID 1686424 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:13]([CH3:18])[C:14]([O:16]C)=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.Br>C(O)(=O)C.[OH-].[Na+]>[OH:2][C:3]1[CH:4]=[C:5]([CH:13]([CH3:18])[C:14]([OH:16])=[O:15])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 66734169Methyl 2-[3-methoxy-5-(trifluoromethyl)phenyl]propanoate

Product 1

HCID 667340972-[3-Hydroxy-5-(trifluoromethyl)phenyl]propanoic acidYield 70%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
100 °C

Procedure

The product from step (ii) (0.8 g) was dissolved in glacial acetic acid (20 ml) and treated with 48% aqueous HBr (20 ml). The mixture was heated at 100° C. for 16 h. The mixture was cooled and diluted with 2M NaOH, extracted with ethyl acetate, dried (MgSO4) and evaporated under reduced pressure to give an oil, which was purified by RPHPLC to give a colourless oil (0.5 g).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure
  5. customto give an oil, which
  6. customwas purified by RPHPLC

Sources & evidence

ORD record
ord-9b82a0e8a97c492b9a6bc35743ac3cbc
Source dataset
uspto-grants-2012_04
Patent number
US08148572B2

Reaction notes

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