Hydrogen Bromide → 4-Hydroxy-2-(trifluoromethyl)phenylacetic acid

HRID 1497495Notes

Reaction equation

HRID 1497495 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[C:5]([C:13]([F:16])([F:15])[F:14])[CH:4]=1.Br>C(O)(=O)C>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[C:5]([C:13]([F:14])([F:15])[F:16])[CH:4]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 467375752-(4-Methoxy-2-(trifluoromethyl)phenyl)acetic acid

Product 1

HCID 846852974-Hydroxy-2-(trifluoromethyl)phenylacetic acidYield 63.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
145 °C

Procedure

To a solution of 4-methoxy-2-(trifluoromethyl)phenylacetic acid (500 mg) in acetic acid (5.00 mL) was added a 48% aqueous hydrobromic acid solution (5.00 mL), followed by stirring at 145° C. overnight. The reaction suspension was concentrated under reduced pressure, to the residue was then added water, and the resulting solid was collected by filtration to obtain 4-hydroxy-2-(trifluoromethyl)phenylacetic acid (300 mg).

Workup

  1. concentrationThe reaction suspension was concentrated under reduced pressure, to the residue
  2. filtrationadded water, and the resulting solid was collected by filtration

Sources & evidence

ORD record
ord-091c0d1e38d74969933e7ad42515a36f
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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