3,4,5-Trimethoxybenzoic Acid → 2-Bromo-3,4,5-trimethoxybenzoic acid

HRID 48085

Reaction equation

HRID 48085 reaction equation
[Br:1]Br.[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([O:16][CH3:17])[C:13]=1[O:14][CH3:15])[C:8]([OH:10])=[O:9]>C(O)(=O)C>[Br:1][C:11]1[C:12]([O:16][CH3:17])=[C:13]([O:14][CH3:15])[C:5]([O:4][CH3:3])=[CH:6][C:7]=1[C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 83573,4,5-Trimethoxybenzoic AcidHCID 24408Bromine

Product 1

HCID 3130972-Bromo-3,4,5-trimethoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of bromine (100 mmol) in 100 mL of acetic acid is added dropwise to a solution of 3,4,5-trimethoxybenzoic acid (100 mmol) in 100 mL of acetic acid cooled by an ice water bath. After the red color of the resulting mixture is discharged, the mixture is poured onto 500 g of crushed ice. The resulting solid is collected by filtration, dried over P2O5 in vacuo, and recrystallized from Et2O to give the product as a pale yellow solid.

Workup

  1. temperaturecooled by an ice water bath
  2. filtrationThe resulting solid is collected by filtration
  3. dry with materialdried over P2O5 in vacuo
  4. customrecrystallized from Et2O

Sources & evidence

ORD record
ord-b83e621f8de54011ba0a2acf013a775e
Source dataset
uspto-grants-2004_03
Patent number
US06702705B1

Linked notes

Loading…