Thionyl Chloride → 4,4,5,5,5-Pentafluoropentane-1-sulfonyl chloride

To a solution of 1,1,1,2,2-pentafluoro-5-p-toluenesulfonyloxypentane (11.0 g, 3.0 mmol) in acetone (10 nm) was added LiBr (523 mg, 6.02 mmol), which was then heated under reflux for 4 hours. After the reaction solution was filtered, the solvent was removed under reduced pressure. The residue thus obtained was dissolved in water (10 ml), Na2SO3 (759 mg, 6.02 mmol) was added thereto, and the resulting mixture was heated under reflux for 17 hours. After the reaction was completed, to the residue which was obtained by removing the solvent under reduced pressure was added EtOH. This mixture was filtered while hot, and the filtrate was concentrated under reduced pressure. The residue was dissolved in benzene (5 ml), DMF (0.5 ml) and thionyl chloride (0.383 ml, 5.25 mmol) were added thereto, and the mixture was heated under reflux overnight. After the reaction was completed, saturated aqueous NaHCO3 solution was added. The resulting mixture was then extracted with methylene chloride and washed with saturated saline solution. The organic layer was dried over magnesium sulfate, and the solvent was removed under reduced pressure. The residue was subjected to silica gel column chromatography (n-hexane:ethyl acetate=10:1) to give 4,4,5,5,5-pentafluoropentylsulfonyl chloride (267 mg, yield 34%).

1. temperaturewas then heated
2. temperatureunder reflux for 4 hours
3. filtrationAfter the reaction solution was filtered
4. customthe solvent was removed under reduced pressure
5. customThe residue thus obtained
6. temperaturethe resulting mixture was heated
7. temperatureunder reflux for 17 hours
8. customwas obtained
9. customby removing the solvent under reduced pressure
10. additionwas added EtOH
11. filtrationThis mixture was filtered while hot, and the filtrate
12. concentrationwas concentrated under reduced pressure
13. dissolutionThe residue was dissolved in benzene (5 ml)
14. temperaturethe mixture was heated
15. temperatureunder reflux overnight
16. extractionThe resulting mixture was then extracted with methylene chloride
17. washwashed with saturated saline solution
18. dry with materialThe organic layer was dried over magnesium sulfate
19. customthe solvent was removed under reduced pressure

ORD record

ord-89e88c229a15409b8296198e61101a6b

Source dataset

uspto-grants-2006_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07074819B2