Water → 6-Bromo-3,4-dimethoxybenzaldehyde

HRID 1740649Notes

Reaction equation

HRID 1740649 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=[O:7].[Br:13]Br.O>C(O)(=O)C>[Br:13][C:8]1[C:5]([CH:6]=[O:7])=[CH:4][C:3]([O:2][CH3:1])=[C:10]([O:11][CH3:12])[CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8419VeratraldehydeHCID 24408Bromine2×

Product 1

HCID 793516-Bromo-3,4-dimethoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3,4-Dimethoxybenzaldehyde (398.8 g) is dissolved in acetic acid (1.8 liter), and thereto is added dropwise bromine (136 ml) at room temperature over a period of four hours. The mixture is stirred overnight, and thereto is added dropwise slowly again bromine (60 ml), and the mixture is stirred overnight. The reaction solution is added to water (7 liters), and the precipitated crystals are collected by filtration, washed with water, and dissolved in chloroform (2 liters). The chloroform solution is washed, dried, concentrated, and the residue is crystallized from diisopropyl ether to give 6-bromo-3,4-dimethoxybenzaldehyde (470 g) as a colorless crystal.

Workup

  1. stirringthe mixture is stirred overnight
  2. filtrationthe precipitated crystals are collected by filtration
  3. washwashed with water
  4. dissolutiondissolved in chloroform (2 liters)
  5. washThe chloroform solution is washed
  6. customdried
  7. concentrationconcentrated
  8. customthe residue is crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-1ab4a51b203941568b0a47b52180330d
Source dataset
uspto-grants-1999_10
Patent number
US05969140

Reaction notes

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