Hydrochloric Acid → 1-(3-fluoro-4-methoxyphenyl)propan-2-one

HRID 1731581Notes

Reaction equation

HRID 1731581 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([CH:11]=[C:12]([N+]([O-])=O)[CH3:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[O:17]1CCCC1>[Fe]>[F:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12](=[O:17])[CH3:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 54314120HCID 54314120, compound

Product 1

HCID 202280021-(3-fluoro-4-methoxyphenyl)propan-2-one

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

Concentrated hydrochloric acid (30 ml) was added dropwise, over 45 minutes, to a stirred mixture of iron powder (6 g) and 1-(3-fluoro-4-methoxyphenyl)-2-nitroprop-1-ene (5.7 g) in tetrahydrofuran (100 ml) at reflux. The mixture was heated under reflux for a further two hours, cooled, filtered and evaporated. Water (100 ml) was added to the residue and extracted with dichloromethane. The dried (magnesium sulphate) extracts were evaporated to dryness to give the title compound as an oil.

Workup

  1. temperatureat reflux
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for a further two hours
  4. temperaturecooled
  5. filtrationfiltered
  6. customevaporated
  7. additionWater (100 ml) was added to the residue
  8. extractionextracted with dichloromethane
  9. dry with materialThe dried (magnesium sulphate) extracts
  10. customwere evaporated to dryness

Sources & evidence

ORD record
ord-4f24f1be4ad34e689f1f0714fbfa20f4
Source dataset
uspto-grants-1986_11
Patent number
US04622342

Reaction notes

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