Hydrochloric Acid → (3,3,4,4,4-Pentafluorobutylthio)acetonitrile

To a suspension of 22.85 g of potassium thioacetate in 200 ml of methanol was added dropwise 54.79 g of 1-iodo-3,3,4,4,4-pentafluorobutane at 0° C. over 30 minutes under a nitrogen atmosphere, and the mixture was stirred at room temperature for 1 hour. At this time, the reaction mixture was analyzed by thin layer chromatography (TLC), and thereby the formation of 3,3,4,4,4-pentafluorobutyl thioacetate was confirmed. After the mixture was cooled to 0° C., 40.52 g of a 28% solution of sodium methoxide in methanol was added dropwise over 15 minutes thereto. The mixture was stirred at room temperature for 1 hour. To the mixture was added 16.61 g of chloroacetonitrile at 0° C., and the mixture was stirred at room temperature for 3 hours. A reaction vessel was cooled in an ice bath, and an aqueous 1N hydrochloric acid solution was added to the reaction mixture. Methanol was distilled off under reduced pressure. The residual reaction mixture was extracted with 200 ml of t-butyl methyl ether twice. Organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried over sodium sulfate, filtered, and then subjected to reduced pressure to distill off the solvent. The residue was subjected to silica gel column chromatography to obtain 17.81 g of (3,3,4,4,4-pentafluorobutylthio)acetonitrile.

1. temperatureAfter the mixture was cooled to 0° C.
2. stirringThe mixture was stirred at room temperature for 1 hour
3. stirringthe mixture was stirred at room temperature for 3 hours
4. temperatureA reaction vessel was cooled in an ice bath
5. distillationMethanol was distilled off under reduced pressure
6. customThe residual reaction mixture
7. extractionwas extracted with 200 ml of t-butyl methyl ether twice
8. washwashed with an aqueous saturated sodium chloride solution
9. dry with materialdried over sodium sulfate
10. filtrationfiltered
11. distillationto distill off the solvent

ORD 기록

ord-ddd0bf009bf547838ec1992b34a84208

출처 데이터셋

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08247596B2