Water → 5-Bromo-3-chloro-2-hydroxy-4-methoxybenzoic acid

HRID 629381Notes

Reaction equation

HRID 629381 reaction equation
[Cl:1][C:2]1[C:3]([OH:13])=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6].[Br:14]Br.O>C(O)(=O)C>[Br:14][C:9]1[C:10]([O:11][CH3:12])=[C:2]([Cl:1])[C:3]([OH:13])=[C:4]([CH:8]=1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 847769843-Chloro-2-hydroxy-4-methoxybenzoic acid

Product 1

HCID 1184681135-Bromo-3-chloro-2-hydroxy-4-methoxybenzoic acidYield 67.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3-chloro-2-hydroxy-4-methoxybenzoic acid (11.1 g) in acetic acid (275 mL) was added bromine (8.79 g) at room temperature, and the mixture was stirred for 16 hr. To the reaction mixture was added water, and the precipitate was collected by filtration. The precipitate was washed with water, and dissolved in ethyl acetate, and the solution was washed with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (10.4 g).

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washThe precipitate was washed with water
  3. dissolutiondissolved in ethyl acetate
  4. washthe solution was washed with water and saturated brine
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c0169a4f5e5149f38c2f2c304e110a3b
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

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