Vinylidene fluoride → (1-Fluorovinyl)dimethylphenylsilane

To a suspension of 4.4 g of lithium wire cut into small pieces in 200 mL of anhydrous THF stirred under argon and cooled on ice (internal temperature <10° C.) was added dimethylphenyl-chlorosilane in 5 mL portions over 1 hour. The deep red color of the silyl lithium reagent appeared after approximately 0.75 hour. The mixture was stirred on ice for an additional 5 hours (internal temperature remained between 5° C. and 10° C.). The mixture was cooled on a dry ice/acetone bath and 1,1-difluoroethylene was introduced by filling a balloon connected to the reaction mixture and the reagent cylinder using a three-way valve. The balloon was filled with 1,1-difluoroethylene and emptied into the reaction mixture 10 times. The mixture was allowed to warm to room temperature (effervescence observed, probably from unreacted 1,1-difluoroethylene). The mixture was diluted with 200 mL of hexanes and filtered through a cotton wool plug. The filtrate was washed with water, dried, filtered, and concentrated in vacuo. Four fractional distillations under vacuum through a Vigreux column gave 4.6 g of product.

1. temperaturecooled on ice (internal temperature <10° C.)
2. stirringThe mixture was stirred on ice for an additional 5 hours (internal temperature remained between 5° C. and 10° C.)
3. temperatureThe mixture was cooled on a dry ice/acetone bath
4. filtrationfiltered through a cotton wool plug
5. washThe filtrate was washed with water
6. customdried
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD-Eintrag

ord-22e73bbb78f740d786a181cd35b9046a

Quelldatensatz

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08741897B2