Methanol → 1-Bromo-2-(dimethoxymethyl)-4,5-dimethoxybenzene

HRID 1743033Notes

Reaction equation

HRID 1743033 reaction equation
[Br:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([O:12][CH3:13])[CH:3]=1.[CH:14]([O-])([O-])[O:15]C.[CH3:19]O>>[CH3:19][O:9][CH:8]([O:15][CH3:14])[C:7]1[C:2]([Br:1])=[CH:3][C:4]([O:12][CH3:13])=[C:5]([O:10][CH3:11])[CH:6]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 793516-Bromo-3,4-dimethoxybenzaldehydeHCID 53629101Methylorthoformate

Product 1

HCID 110771461-Bromo-2-(dimethoxymethyl)-4,5-dimethoxybenzeneYield 93.9%

Procedure

6-Bromo-3,4-dimethoxybenzaldehyde (470 g) is suspended in methanol (600 ml), and thereto are added methyl ortho-formate (1025 ml) and IRA-120 (H+-type) (10 g), and the mixture is refluxed for one hour. The mixture is cooled to room temperature, and the insoluble materials are removed by filtration. The filtrate is concentrated under reduced pressure, and the resulting residue is dissolved in diethyl ether. The mixture is washed, dried, and evaporated to remove the diethyl ether. The resulting residue is distilled under reduced pressure to give 6-bromo-3,4-dimethoxybenzaldehyde dimethylacetal (522 g) as main distillate (133°-138° C./1Torr).

Workup

  1. temperaturethe mixture is refluxed for one hour
  2. customthe insoluble materials are removed by filtration
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. dissolutionthe resulting residue is dissolved in diethyl ether
  5. washThe mixture is washed
  6. customdried
  7. customevaporated
  8. customto remove the diethyl ether
  9. distillationThe resulting residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-ffc0aa98115c465a825610873af9afdf
Source dataset
uspto-grants-1994_08
Patent number
US05342941

Reaction notes

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