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

HRID 908058Notes

Reaction equation

HRID 908058 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-caa95a4df993405394fc564d95655698
Source dataset
uspto-grants-2011_09
Patent number
USRE042700E1

Reaction notes

Loading…