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

HRID 1826613Notes

Reaction equation

HRID 1826613 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[Br:11]Br>C(O)(=O)C>[Br:11][C:10]1[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=1[OH:1]

Participants

4

Reactant 2

HCID 74203-Hydroxybenzoic AcidHCID 24408Bromine

Product 1

HCID 64209734-Bromo-3-hydroxybenzoic acidYield 19,199.699%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 3-hydroxybenzoic acid 5 (18.2 g, 0.132 mol) in 180 ml of glacial acetic acid cooled in a water bath was slowly added over a period of 2 h bromine (21.1 g, 0.132 mmol) in 70 ml of acetic acid. The solution was stirred overnight. After removing bromine and 160 ml of acetic acid under reduced pressure, the mixture was cooled to 0° C., filtered, washed (50 ml of cold water), and dried under vacuum to give a white solid. Crystallization (H2O) gave 4-bromo-3-hydroxybenzoic acid as white crystals (5.5 g, 19%).

Workup

  1. customAfter removing bromine and 160 ml of acetic acid under reduced pressure
  2. filtrationfiltered
  3. washwashed (50 ml of cold water)
  4. customdried under vacuum
  5. customto give a white solid
  6. customCrystallization (H2O)

Sources & evidence

ORD record
ord-cfed9dcdaac24c2488d5f7363f85e2f0
Source dataset
uspto-grants-2006_05
Patent number
US07053071B2

Reaction notes

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