Trifluoromethanesulfonic anhydride → HCID 58879040, compound

HRID 1443592Notes

Reaction equation

FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.[F:16][C:17]([F:30])([C:20]([F:29])([F:28])[C:21]([F:27])([F:26])[C:22]([F:25])([F:24])[F:23])[CH2:18]O>>[F:13][C:10]([F:11])([F:12])[S:7]([O:6][CH2:18][C:17]([F:16])([F:30])[C:20]([F:28])([F:29])[C:21]([F:26])([F:27])[C:22]([F:25])([F:24])[F:23])(=[O:8])=[O:9]

Participants

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydride

HCID 27823941H,1H-Perfluoro-1-pentanol

Product 1

HCID 58879040HCID 58879040, compoundYield 61.5%

Conditions

Temperature: 100 °C

Procedure

6.8 g of trifluoromethanesulfonic anhydride was added dropwise to 5.0 g of 2,2,3,3,4,4,5,5,5-nonafluoropentanol at 0° C., and the mixture was stirred at room temperature for 5 hours and at 100° C. for 3 hours. Thereafter, the reaction mixture was poured to ice water and then extracted with methyl tert-butyl ether. The organic layer was washed successively with water, aqueous saturated sodium hydrogen carbonate and aqueous saturated sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 4.7 g of 2,2,3,3,4,4,5,5,5-nonafluoropentyl trifluoromethanesulfonate.

Workup

extractionextracted with methyl tert-butyl ether
washThe organic layer was washed successively with water, aqueous saturated sodium hydrogen carbonate and aqueous saturated sodium chloride
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-f17c23273cdb4a4fbb0bd04f39dd84ce
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07662402B2

Reaction notes

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