Acetone → 1-(5-Bromo-2-methoxy-3-nitrophenyl)ethan-1-one

HRID 1295965Notes

Reaction equation

HRID 1295965 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[CH3:15]OS(=O)(=O)OC.C(=O)([O-])[O-].[K+].[K+].CC(C)=O>C(OCC)(=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]([O:11][CH3:15])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 6890715'-Bromo-2'-hydroxy-3'-nitroacetophenone

Product 1

HCID 229296971-(5-Bromo-2-methoxy-3-nitrophenyl)ethan-1-oneYield 88.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the 1-(5-bromo-2-hydroxy-3-nitrophenyl)-1-ethanone (17.4 g), dimethylsulfuric acid (12.7 g), potassium carbonate (13.8 g) and acetone (200 mL) was heated to reflux for 15 hours, and then water was added to the mixture and extraction was performed with ethyl acetate. The organic layer was washed with brine and then dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (16.2 g) as a yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 15 hours
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter distilling off the solvent under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-c573ce16fa364af2b008377b484d6d15
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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