4-Hydroxybenzoic Acid → 3-Bromo-4-hydroxybenzoic acid

HRID 1577053Notes

Reaction equation

HRID 1577053 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[Br:11]Br.O>C(O)(=O)C>[Br:11][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:2]=1[OH:1])[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 1354-Hydroxybenzoic AcidHCID 962WaterHCID 24408Bromine

Product 1

HCID 843683-Bromo-4-hydroxybenzoic acidYield 70.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

50 g (0.37 mol) of commercially available p-hydroxybenzoic acid was dissolved in 370 ml glacial acetic acid by heating with stirring. Heating was continued after the acid dissolved and 59 g (0.37 mol) bromine dissolved in 60 ml glacial acetic acid was rapidly added to the boiling solution to avoid bumping. The solution was refluxed for six hours with continuing stirring. Following reflux, the reaction solution was permitted to stand and cooled to room temperature. The cooled solution was poured into two liters of cold water. A white precipitate was formed. The white crystals were filtered by suction and were recrystalized with glacial acetic acid to yield 55.2 g of purified 3-bromo-4-hydroxybenzoic acid. The calculated yield was 70.3%.

Workup

  1. temperatureby heating
  2. temperatureHeating
  3. dissolutiondissolved
  4. additionwas rapidly added to the boiling solution
  5. temperatureThe solution was refluxed for six hours
  6. stirringwith continuing stirring
  7. temperatureFollowing reflux
  8. customA white precipitate was formed
  9. filtrationThe white crystals were filtered by suction
  10. customwere recrystalized with glacial acetic acid

Sources & evidence

ORD record
ord-dd802689f0164566bfe2c5ca966d1a83
Source dataset
uspto-grants-1981_09
Patent number
US04287085

Reaction notes

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