Reaction #1563930

Reaction equation

4-chloro-1-(2,5-difluorophenyl)butan-1-one

(S)-2-methylpropane-2-sulfinamide

→

title compound

Yield 86.4%

(S,E)-N-(4-chloro-1-(2,5-difluorophenyl)butylidene)-2-methylpropane-2-sulfinamide

Yield 86.4%

Solvents

THF

Conditions

Workup

1. 1
   workup.STIRRINGThe mixture was stirred continuously at 70° C. for 16 h
2. 2
   OtherReaction mixture
3. 3
   Otherquenched with saturated aqueous NH4Cl solution
4. 4
   workup.ADDITIONdiluted with ethylacetate
5. 5
   Filtrationfiltered
6. 6
   WashThe filtrate was washed with water
7. 7
   OtherThe organic layer was separated
8. 8
   Dryingdried over anhydrous sodium sulfate
9. 9
   Concentrationconcentrated under reduced pressure

Procedure

Titanium (IV) ethoxide (54.77 g, 240.13 mmol) was added to a solution of 4-chloro-1-(2,5-difluorophenyl)butan-1-one (35 g, 160.09 mmol) and (S)-2-methylpropane-2-sulfinamide (29.1 g, 240.13 mmol) in THF (400 mL) with stirring. The mixture was stirred continuously at 70° C. for 16 h. Reaction mixture was then cooled to a temperature of 20-35° C., quenched with saturated aqueous NH4Cl solution, diluted with ethylacetate and filtered. The filtrate was washed with water followed by brine solution. The organic layer was separated, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 44.5 g of the title compound as a colourless liquid.

Source