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

HRID 1384050

Reaction equation

HRID 1384050 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-4251066a793447ee9e4d8ca065c1be2c
Source dataset
uspto-grants-2001_07
Patent number
US06258360B1

Linked notes

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