Water → 2-Bromo-5-hydroxybenzoic acid

HRID 963625Notes

Reaction equation

HRID 963625 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([O:11]C)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].B(Br)(Br)Br.O>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromide2×HCID 899062-Bromo-5-methoxybenzoic acid

Product 1

HCID 122494352-Bromo-5-hydroxybenzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-60 °C

Procedure

A mixture of 2-bromo-5-methoxybenzoic acid (10 g, 0.043 mol) in methylene chloride is cooled to -60° C., treated with boron tribromide (3.59 g, 0.143 mol), stirred at -60° C. for 1 hour, stirred at room temperature for 1 hour, cooled to -70° C., treated with additional boron tribromide (3.59 g, 0.143 mol), stirred at -70° C. for 1 hour, stirred at room temperature for 1 hour and poured into water. The aqueous mixture is extracted with ethyl acetate. The organic extracts are combined, washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title product as a white solid which is identified by 1H and 13CNMR spectral analyses.

Workup

  1. stirringstirred at room temperature for 1 hour
  2. temperaturecooled to -70° C.
  3. stirringstirred at -70° C. for 1 hour
  4. stirringstirred at room temperature for 1 hour
  5. extractionThe aqueous mixture is extracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-df71e8ecff0743169c9eddf75b4e0b97
Source dataset
uspto-grants-1998_06
Patent number
US05763605

Reaction notes

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