Methanol → 1,3-Dibromo-5-(dimethoxymethyl)benzene

HRID 487069Notes

Reaction equation

HRID 487069 reaction equation
[Br:1][C:2]1[CH:3]=C([CH:7]=[C:8]([Br:10])[CH:9]=1)C=O.CO.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:24][O:25][C:26]([O:29][CH3:30])(C)[CH3:27]>>[Br:1][C:2]1[CH:3]=[C:27]([CH:26]([O:29][CH3:30])[O:25][CH3:24])[CH:7]=[C:8]([Br:10])[CH:9]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 6220773,5-Dibromobenzaldehyde

Product 1

HCID 190934581,3-Dibromo-5-(dimethoxymethyl)benzene

Procedure

A mixture of 13.2 g (50 mmoles) of crude 3,5-dibromobenzaldehyde, 2 mL (50 mmoles) of methanol, and 100 mg of p-toluenesulfonic acid in 100 mL of 2,2-dimethoxypropane was heated to reflux 6 hrs. After cooling, solvent was removed in vacuo to give a brown oil. This was applied on silica gel and washed with 1:20 ethylacetate:hexane mixture. The filtrate was concentrated to orange brown oil of the desired acetal.

Workup

  1. temperaturewas heated
  2. temperatureto reflux 6 hrs
  3. temperatureAfter cooling
  4. customsolvent was removed in vacuo
  5. customto give a brown oil
  6. washwashed with 1:20 ethylacetate
  7. concentrationThe filtrate was concentrated to orange brown oil of the desired acetal

Sources & evidence

ORD record
ord-0753b49967b745219b0540d7f65c6bd8
Source dataset
uspto-grants-1994_03
Patent number
US05294610

Reaction notes

Loading…