Selenium Dioxide → HCID 22273591, compound

HRID 1064271Notes

Reaction equation

HRID 1064271 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6]([Br:11])[CH:5]=1)=[O:3].[Se](=O)=[O:13]>O1CCOCC1.O>[Br:11][C:6]1[CH:5]=[C:4]([C:2](=[O:3])[CH:1]=[O:13])[CH:9]=[CH:8][C:7]=1[F:10]

Participants

5

Reactant 2

HCID 24007Selenium DioxideHCID 705081-(3-Bromo-4-fluorophenyl)ethan-1-one

Product 1

HCID 22273591HCID 22273591, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To 3-bromo-4-fluoroacetophenone (11.0 g) in 1,4-dioxane (160 ml) and water (15 ml) was added selenium dioxide (8.8 g). The mixture was heated at reflux for 10 h, cooled to room temperature, and the solvent then removed at reduced pressure. The residue was suspended in 50% diethyl ether in isohexane, and residual solid removed by filtration. The filtrate was dried over Na2SO4, and solvent then evaporated to give (3-bromo-4-fluorophenyl)oxoacetaldehyde as a yellow oil, which was used without further purification in the next step.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 10 h
  3. customthe solvent then removed at reduced pressure
  4. customresidual solid removed by filtration
  5. dry with materialThe filtrate was dried over Na2SO4, and solvent
  6. customthen evaporated

Sources & evidence

ORD record
ord-63a23e25a931414c84ab52f909c78514
Source dataset
uspto-grants-2005_11
Patent number
US06969716B2

Reaction notes

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