Bromide ion → (4-Chloro-2-hydroxyphenoxy)acetic acid

HRID 11614Notes

Reaction equation

HRID 11614 reaction equation
[Br-].[Cl:2][C:3]1[CH:13]=[CH:12][C:6]([O:7][CH2:8][C:9]([OH:11])=[O:10])=[C:5]([O:14]C)[CH:4]=1>O>[Cl:2][C:3]1[CH:13]=[CH:12][C:6]([O:7][CH2:8][C:9]([OH:11])=[O:10])=[C:5]([OH:14])[CH:4]=1

Participants

4

Reactant 2

HCID 259Bromide ionHCID 116585842-(4-Chloro-2-methoxyphenoxy)acetic acid

Product 1

HCID 16748825(4-Chloro-2-hydroxyphenoxy)acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 48% aqueous hyrdrogen bromide (20 mL) was added (4-chloro-2-methoxy-phenoxy)-acetic acid (2.1 g, 9.7 mmol). The resulting mixture was heated to reflux overnight. The mixture was cooled to ambient temperature, diluted with water and extracted with diethyl ether. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo to give (4-chloro-2-hydroxy-phenoxy)-acetic acid. The crude product was added to a solution of pyridinium p-toluene sulfonate (0.10 g, 0.40 mmol) in toluene (100 mL). The resulting mixture was heated to reflux for five hours. The reaction was allowed to cool to ambient temperature and concentrated in vacuo. Chromatography on silica gel gave the title compound (0.97 g).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux overnight
  3. extractionextracted with diethyl ether
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a62f0d2dcbcb40f2a0c77212a8c65747
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Reaction notes

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