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

HRID 335435Notes

Reaction equation

HRID 335435 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-ethanone

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) (4.8.1 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) 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)

Sources & evidence

ORD record
ord-d69d6367ce7c4a9f8ee96be6fab9bc96
Source dataset
uspto-grants-2014_11
Patent number
US08884010B2

Reaction notes

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