Water → 2-Bromo-5-methoxybenzoic acid

HRID 1586136Notes

Reaction equation

HRID 1586136 reaction equation
[C:1]([OH:11])(=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=1.[Br:12]Br.O>C(O)(=O)C>[Br:12][C:7]1[CH:6]=[CH:5][C:4]([O:8][CH3:9])=[CH:3][C:2]=1[C:1]([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 962WaterHCID 114613-Methoxybenzoic AcidHCID 24408Bromine

Product 1

HCID 899062-Bromo-5-methoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To m-anisic acid in acetic acid (1 L) is added dropwise bromine (85 ml), followed by water (1 L). The reaction mixture is heated to reflux, cooled in an ice-bath and then the product is collected by filtration, washed with cold water and dried to afford 2-bromo-5-methoxybenzoic acid, m.p. 154°-156° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux
  3. temperaturecooled in an ice-bath
  4. filtrationthe product is collected by filtration
  5. washwashed with cold water
  6. customdried

Sources & evidence

ORD record
ord-8d046ca980d34776adde257706b20740
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

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