Water → 2-Bromo-5-methoxybenzoic acid

HRID 1377789Notes

Reaction equation

HRID 1377789 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 acidYield 79%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of m-anisic acid (250 g, 1.67 mol) in acetic acid (1 L) was added bromine (85 mL) and then water (1L). The mixture was heated to reflux, cooled in an ice bath and the product which precipitated was collected by filtration and washed with water to afford 305.7 g (79%) of 2-bromo-5-methoxybenzoic acid, m.p. 154°-156° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperaturecooled in an ice bath
  4. customthe product which precipitated
  5. filtrationwas collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-19b33d4ddd0144388c8e67d75f96f764
Source dataset
uspto-grants-1997_09
Patent number
US05665760

Reaction notes

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