Sulfur trioxide → Difluoromalonyl fluoride

HRID 1680420Notes

Reaction equation

HRID 1680420 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

3

Reactant 2

HCID 24682Sulfur trioxideHCID 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

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

Sources & evidence

ORD record
ord-325d9b4ab01649eb8e2c2eedd0c4cd92
Source dataset
uspto-grants-1981_06
Patent number
US04273729

Reaction notes

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