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

HRID 324033

Reaction equation

HRID 324033 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-311d3a0a51d0408b98f9608191981361
Source dataset
uspto-grants-2001_04
Patent number
US06214996B1

Linked notes

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