1-(3-Fluoro-4-methoxyphenyl)ethan-1-one → 3-Fluoro-4-methoxy-alpha-oxobenzeneacetaldehyde

HRID 2260111Notes

Reaction equation

HRID 2260111 reaction equation
[Se]=[O:2].[CH3:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([F:14])[CH:7]=1)=[O:5]>O1CCOCC1>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([C:4](=[O:5])[CH:3]=[O:2])=[CH:7][C:8]=1[F:14]

Participants

4

Reactant 2

HCID 968281-(3-Fluoro-4-methoxyphenyl)ethan-1-oneHCID 167175Oxyselenide

Product 1

HCID 129217133-Fluoro-4-methoxy-alpha-oxobenzeneacetaldehyde

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Selenium oxide (4.953 g) is heated to dissolve in 100 ml aqueous dioxane (95:5 dioxane: H2O). The 3-fluoro-4-methoxyacetophenone (5.00 g) is added to the mixture. The resulting mixture is refluxed overnight then coiled. The precipitated selenium metal is filtered. The filtrate is concentrated in vacuo to give a brown thick gum. It is recrystallized from -~200 ml hot H2O, filtered hot and allowed to stand at RT overnight. The precipitated pale pink flake are filtered, washed with H2O and let air dried to give 1-methoxy-2-fluoro-4-glyoxyloylbenzene, which is used directly in the next step.

Workup

  1. temperatureThe resulting mixture is refluxed overnight
  2. filtrationThe precipitated selenium metal is filtered
  3. concentrationThe filtrate is concentrated in vacuo
  4. customto give a brown thick gum
  5. customIt is recrystallized from -~200 ml hot H2O
  6. filtrationfiltered hot
  7. filtrationThe precipitated pale pink flake are filtered
  8. washwashed with H2O
  9. customdried

Sources & evidence

ORD record
ord-6bb8e1024614435caf1851fd926bd2a9
Source dataset
uspto-grants-1995_12
Patent number
US05476851

Reaction notes

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