Reaction #666431

Reaction equation

sodium methanesulfinate

4-fluorophenacyl chloride

ethanol

→

1-(4-fluorophenyl)-2-methylsulfonylethan-1-one

Yield 86.1%

Solvents

water

Conditions

Workup

1. 1
   Temperatureheated
2. 2
   Temperatureto reflux for 1 hour
3. 3
   FiltrationThe precipitated solids were collected by filtration
4. 4
   Washwashed with water
5. 5
   Otherdried
6. 6
   workup.DISSOLUTIONThe solids were dissolved in ethyl acetate
7. 7
   Dryingdried over anhydrous sodium sulfate
8. 8
   Concentrationconcentrated under reduced pressure
9. 9
   OtherThe resulting residue was purified by recrystallization (hexane—ethyl acetate) acetate)

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).

Source