Ethanol → 1-(4-Fluorophenyl)-2-(methylsulfonyl)-1-ethanone

HRID 579249Notes

Reaction equation

HRID 579249 reaction equation
[CH3:1][S:2]([O-:4])=[O:3].[Na+].[F:6][C:7]1[CH:16]=[CH:15][C:10]([C:11](=[O:14])[CH2:12]Cl)=[CH:9][CH:8]=1.C(O)C>O>[F:6][C:7]1[CH:16]=[CH:15][C:10]([C:11](=[O:14])[CH2:12][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 1202482-Chloro-4'-fluoroacetophenoneHCID 2733271Sodium methanesulfinate

Product 1

HCID 14882461-(4-Fluorophenyl)-2-(methylsulfonyl)-1-ethanoneYield 86.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 1 L volume four-necked flask, sodium methanesulfinate (31.3 g), 4-fluorophenacyl chloride (21-b) (48.1 g), and ethanol (300 ml) were added under a nitrogen atmosphere, and heated to reflux for 1 hour. After the mixture was cooled to room temperature, water (500 ml) was added. The precipitated solids were collected by filtration, washed with water, and dried. The solids were dissolved in ethyl acetate, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by recrystallization (hexane—ethyl acetate) acetate) to give 51.9 g of 1-(4-fluorophenyl)-2-methylsulfonylethan-1-one (7-2-3).

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. filtrationThe precipitated solids were collected by filtration
  4. washwashed with water
  5. customdried
  6. dissolutionThe solids were dissolved in ethyl acetate
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was purified by recrystallization (hexane—ethyl acetate) acetate)

Sources & evidence

ORD record
ord-1010ceadbac94158bd05e55250759a0f
Source dataset
uspto-grants-2015_05
Patent number
US09040709B2

Reaction notes

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