Cesium fluoride → Acetic acid, fluorooxo-, 2-chloro-2-propenyl ester

Under dry N2 in flame dried glass apparatus, cesium fluoride (167 g, 1.1 mol) was placed in a 1 liter single neck flask and placed under high vacuum and gently heated with a flame until the solid became free flowing, then cooled to room temperature. Acetonitrile, distilled from CaH2 (183 ml) was added and the mixture cooled to -20° C. internal temperature. 2-Chloroallyl oxalochloride (183 g, 1.0 mol) was added dropwise over a 30 minute period and the mixture slowly warmed to room temperature, stirred at that temperature for 16 hours, and byproduct cesium chloride recovered by filtration with acetonitrile wash. The filtrate and wash were combined and stripped, and the residue distilled at reduced temperature to yield 129 g (77%) of the desired product, b.p. 62°-64° C./22 mm.

1. temperatureUnder dry N2 in flame
2. customwas placed in a 1 liter single neck flask
3. temperaturegently heated with
4. temperaturea flame until the solid
5. distillationAcetonitrile, distilled from CaH2 (183 ml)
6. additionwas added
7. temperaturethe mixture cooled to -20° C. internal temperature
8. temperaturethe mixture slowly warmed to room temperature
9. filtrationbyproduct cesium chloride recovered by filtration with acetonitrile
10. washwash
11. washThe filtrate and wash
12. distillationthe residue distilled at reduced temperature

ORD record

ord-0121908d6db04606a175eac1651de591

Source dataset

uspto-grants-1994_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05319103