Acetone → 4-(5-Chloro-2-fluorophenyl)-3-buten-2-one

HRID 1700726Notes

Reaction equation

HRID 1700726 reaction equation
[OH-].[Na+].O.[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([F:13])=[C:9]([CH:12]=1)[CH:10]=O.[CH3:14][C:15]([CH3:17])=[O:16]>>[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([F:13])=[C:9]([CH:10]=[CH:14][C:15](=[O:16])[CH3:17])[CH:12]=1

Participants

5

Reactant 4

HCID 180Acetone2×HCID 962WaterHCID 14798Sodium HydroxideHCID 27735865-Chloro-2-fluorobenzaldehyde

Product 1

HCID 537643824-(5-Chloro-2-fluorophenyl)-3-buten-2-one

Procedure

To a mixture of acetone (22 ml), sodium hydroxide (0.83 g) and water (55 ml) was added dropwise at room temperature a solution of 5-chloro-2-fluorobenzaldehyde (3.5 g) in acetone (20 ml), and the mixture was stirred at the same temperature for 15 hours. Under reduced pressure, acetone was evaporated, and the residue was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and concentrated under reduced pressure to give 4-(5-chloro-2-fluorophenyl)-3-buten-2-one (4.3 g).

Workup

  1. customUnder reduced pressure, acetone was evaporated
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2a526cdeea404ab99e95eb3afa06935c
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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