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

HRID 613030

Reaction equation

HRID 613030 reaction equation
[Br:1][C:2]1[C:7](C=O)=[CH:6][C:5]([O:10][CH3:11])=[C:4]([O:12][CH3:13])[CH:3]=1.[CH:14]([O:19][CH3:20])([O:17][CH3:18])OC>CO>[CH3:20][O:19][CH:14]([O:17][CH3:18])[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 2

HCID 9005Trimethyl orthoformateHCID 793516-Bromo-3,4-dimethoxybenzaldehyde

Product 1

HCID 110771461-Bromo-2-(dimethoxymethyl)-4,5-dimethoxybenzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-Bromo-3,4-dimethoxybenzaldehyde (470 g) is suspended in methanol (600 ml), and thereto are added trimethyl orthoformate (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, and the filtrate is concentrated under reduced pressure. The resulting residue is dissolved in ether, washed, dried, evaporated to remove the ether, and distilled under reduced pressure to give 6-bromo-3,4-dimethoxybenzaldehyde dimethyl acetal (522 g) as a main distillate (133-138° C./1 Torr).

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 ether
  5. washwashed
  6. customdried
  7. customevaporated
  8. customto remove the ether
  9. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-a4faae7e17ca4d15b79f5c74c0c70843
Source dataset
uspto-grants-1999_12
Patent number
US06005106

Linked notes

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