Butyl bromide → Fluorine

Temperature

50 °C

6.3 mL (10 g; 50 mmoles) perfluoroisobutylene (CAUTION! highly toxic) were condensed into a heterogeneous mixture of 7.6 g (50 mmoles) cesium fluoride stirring in 20 mL of dry diglyme. A yellow color developed within the reaction mixture, attributed to carbanion formation. After 2 hours of mild heating (about 50° C.) and stirring, 6.9 g (50 mmoles) 1-bromobutane were added. Upon this addition of alkyl halide, much milky precipitate was observed. The reaction was allowed to stir several hours (about 4 hours), then the low boiling product was isolated by attaching a condenser to the reaction set-up and heating to 150° C. Thus 9.8 g of a clear, colorless liquid were distilled from the crude reaction mixture. Further purification by fractional distillation yielded 8.0 g (58% overall yield) of liquid with a boiling point of 108° C. Confirmation of structure (CF3)3CCH2CH2CH2CH3, was provided by proton and fluorine-19 NMR with supporting data from the chemical literature (Knunyants, I. L., Yakobson, G. G., Synthesis of Fluoroorganic Compounds, Springer-Verlag, N.Y., 1985).

1. customcondensed
2. stirringto stir several hours (about 4 hours)
3. customthe low boiling product was isolated
4. temperatureheating to 150° C
5. distillationThus 9.8 g of a clear, colorless liquid were distilled from the crude
6. customreaction mixture
7. customFurther purification
8. distillationby fractional distillation
9. customyielded
10. custom8.0 g (58% overall yield) of liquid with a boiling point of 108° C

ORD record

ord-27dbf8e0294348c9a28aad5ade8b2d81

Source dataset

uspto-grants-1992_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05116599