Water → 2-Bromo-5-methoxybenzoic acid

HRID 2226211Notes

Reaction equation

HRID 2226211 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-119f0baae879418cbfa8dbba667b7398
Source dataset
uspto-grants-1994_09
Patent number
US05346917

Reaction notes

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