Sulfur trioxide → Difluoromalonyl fluoride

HRID 1680769

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-4aaf57d3b9884f31b0f50d45f0aeebe8
Source dataset: uspto-grants-1981_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04275225

Linked notes

Loading…