Veratraldehyde → 6-Bromo-3,4-dimethoxybenzaldehyde

HRID 2299186Notes

Reaction equation

HRID 2299186 reaction equation
[Br:1]Br.[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[CH:8]=[O:9].S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(O)(=O)C>[Br:1][C:10]1[C:7]([CH:8]=[O:9])=[CH:6][C:5]([O:4][CH3:3])=[C:12]([O:13][CH3:14])[CH:11]=1

Participants

6

Reactant 4

HCID 8419VeratraldehydeHCID 24408BromineHCID 24477Sodium ThiosulfateHCID 516892Sodium Bicarbonate

Product 1

HCID 793516-Bromo-3,4-dimethoxybenzaldehydeYield 56.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of bromine (0.96 g) in acetic acid (10 ml) was dropped into a solution of 3,4-dimethoxybenzaldehyde (1.0 g) in acetic acid (4 ml) and the mixture was stirred for three hours. Sodium thiosulfate was added to the reaction mixture, then sodium bicarbonate was added thereto and the mixture was filtered. The crude crystals collected by the filtration were recrystallized from chloroform-ether to give the title compound (0.83 g, 56%). The peaks of this compound in 1H-NMR (400 MHz, CDCl3) were as follows.

Workup

  1. filtrationthe mixture was filtered
  2. filtrationThe crude crystals collected by the filtration
  3. customwere recrystallized from chloroform-ether

Sources & evidence

ORD record
ord-f31b495198ac413d9e248135b5b87467
Source dataset
uspto-grants-2002_12
Patent number
US06495592B1

Reaction notes

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