Acetic Acid → 4-Bromo-2-hydroxybenzoic acid

HRID 1244775Notes

Reaction equation

HRID 1244775 reaction equation
[OH:1][C:2]1C=[C:4]([CH:8]=[CH:9][CH:10]=1)C(O)=O.[Br:11]Br.[C:13]([OH:16])(=[O:15])[CH3:14]>S(=O)(=O)(O)O.O>[Br:11][C:9]1[CH:8]=[CH:4][C:14]([C:13]([OH:16])=[O:15])=[C:2]([OH:1])[CH:10]=1

Participants

6

Reactant 3

HCID 176Acetic Acid2×HCID 74203-Hydroxybenzoic AcidHCID 24408Bromine

Product 1

HCID 2687374-Bromo-2-hydroxybenzoic acidYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 3-hydroxybenzoic acid (14.480 mmol, 2 g) in acetic acid (14.5 mL) and sulfuric acid (1.5 mL) at 50° C., a solution of bromine (15.204 mmol, 0.780 mL) in acetic acid (7.2 mL) was added and stirred 30 minutes at 100° C. The reaction was allowed to cool to RT and diluted with water. The aqueous layer was extracted with ethyl acetate, washed with water and brine, dried (MgSO4), filtered, and concentrated under reduced pressure to give the 4-bromo-2-hydroxy-benzoic acid. Yield: 100%.

Workup

  1. temperatureto cool to RT
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2baea802e30045c3ac7a296e3da7cee2
Source dataset
uspto-grants-2006_10
Patent number
US07122565B2

Reaction notes

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