Water → 2-Bromo-5-methoxybenzoic acid

HRID 1769184Notes

Reaction equation

HRID 1769184 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 (1 L). 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-c659c5ab75764bb6a86df3f42345e76f
Source dataset
uspto-grants-1995_01
Patent number
US05380749

Reaction notes

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