Sulfur trioxide → Difluoromalonyl fluoride

HRID 1702853

Reaction equation

C[O:2][C:3](F)([F:10])[C:4]([F:9])([F:8])[C:5]([F:7])=[O:6].S(=O)(=O)=O>>[F:8][C:4]([F:9])([C:5]([F:7])=[O:6])[C:3]([F:10])=[O:2]

Participants

Reactant 2

HCID 24682Sulfur trioxide

HCID 136846932,2,3,3-Tetrafluoro-3-methoxypropanoyl fluoride

Product 1

HCID 2774099Difluoromalonyl fluoride

Procedure

3-Methoxytetrafluoropropionyl fluoride (F. S. Fawcett, C. W. Tullock and D. D. Coffman, J. Amer. Chem. Soc., 84, 4275 (1962)) (81 g, 0.45 mol) was slowly added to sulfur trioxide (80 g, 1.0 mol) at 40° C., and the product difluoromalonyl difluoride, bp -9° C., was continuously removed by distillation through a low temperature still, yield 58 g (0.40 mol, 90%). The product structure was confirmed by: λmax 1860 cm-1 (COF), 19F NMR (no solvent), +17.1 ppm (t J=10 Hz) 2F, COF and -114.2 ppm (t J=10 Hz) 2F, CF2.

Workup

customthe product difluoromalonyl difluoride, bp -9° C., was continuously removed by distillation through a low temperature still

Sources & evidence

ORD record: ord-7065c9f392b84b1999c24db01f1d4cc6
Source dataset: uspto-grants-1982_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04349650

Linked notes

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