Sulfuric Acid → 1-Bromo-3-(dimethoxymethyl)benzene

HRID 916683Notes

Reaction equation

HRID 916683 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)[CH:5]=[CH:6][CH:7]=1.OS(O)(=O)=O>CO>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]([O:9][CH3:10])[O:12][CH3:11])[CH:3]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 873062-(3-Bromophenyl)-1,3-dioxolane

Product 1

HCID 1053951-Bromo-3-(dimethoxymethyl)benzeneYield 88.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Commercial 2-(3-Bromo-phenyl)-[1,3]dioxolane (1.3 mL, 8.64 mmol) was dissolved in anhydrous MeOH (40 mL) and catalytic amount of H2SO4 was added. The resulting reaction mixture was stirred 4 h at rt and finally extracted with petroleum ether (3×50 mL). The combined organic phases were washed with NaHCO3 (40 mL), dried (MgSO4), filtered and concentrated under vacuum to give 22b as a colourless oil (1.76 g, 88%), whose spectroscopic data were in close agreement with literature (29).

Workup

  1. customThe resulting reaction mixture
  2. extractionfinally extracted with petroleum ether (3×50 mL)
  3. washThe combined organic phases were washed with NaHCO3 (40 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-32e66d79d850497f94cd15625df312b4
Source dataset
uspto-grants-2007_09
Patent number
US07271186B1

Reaction notes

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