Vinylidene fluoride → HCID 12559149, compound

HRID 1680419Notes

Reaction equation

[O:1]=[C:2]([C:10]([F:13])([F:12])[F:11])[C:3]([F:9])([F:8])[S:4]([OH:7])(=[O:6])=[O:5].[C:14]([F:17])([F:16])=[CH2:15]>>[O:1]=[C:2]([C:10]([F:13])([F:11])[F:12])[C:3]([F:8])([F:9])[S:4]([O:7][C:14]([F:17])([F:16])[CH3:15])(=[O:6])=[O:5]

Participants

Reactant 2

HCID 6369Vinylidene fluoride

HCID 125591471,1,3,3,3-Pentafluoro-2-oxopropane-1-sulfonic acid

Product 1

HCID 12559149HCID 12559149, compoundYield 70%

Conditions

Temperature: 25 °C

Procedure

A metal tube containing 2-oxopentafluoropropanesulfonic acid (23.8 g, 0.10 mol) was cooled below -40° C. and vinylidene fluoride (1,1-difluoroethene) (13 g, 0.20 mol) was added. The mixture was shaken and warmed to 25° C. where it was kept for 4 hours. Distillation of the liquid product gave 20.4 g (0.07 mol, 70%) of 1,1-difluoroethyl 2-oxopentafluoropropanesulfonate, bp 62°-63° C. (50 mm Hg): λmax l (CCl4) 5.54 (C=O), 6.96 (SO2O) and 7.5-9 μm (CF, SO2); 1H NMR, δ2.06 ppm (t J=14.3 Hz) CH3 ; 19F NMR, -58.3 (q J=14.3 Hz, each member t J=7.1 Hz) 2F, OCF2, -75.0 (t J=8.0 Hz) 3F, CF3 and -106.1 ppm (q J= 8.0 Hz, each member t J=7.1 Hz) 2F, CF2SO2.

Workup

temperaturewas cooled below -40° C.
distillationDistillation of the liquid product

Sources & evidence

ORD record: ord-1b0d647b0fe14452a7ddb2d2f1436c91
Source dataset: uspto-grants-1981_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04273729

Reaction notes

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