Iodine → HCID 14203360, compound

HRID 463629Notes

Reaction equation

HRID 463629 reaction equation
[F:1][C:2]([F:25])([O:7][C:8]([F:24])([C:20]([F:23])([F:22])[F:21])[C:9]([F:19])([F:18])[O:10][C:11]([F:17])(Cl)[C:12]([F:15])([F:14])Cl)[C:3]([O:5][CH3:6])=[O:4].II>[Zn].COCCOCCOC>[F:1][C:2]([F:25])([O:7][C:8]([F:24])([C:20]([F:21])([F:22])[F:23])[C:9]([F:19])([F:18])[O:10][C:11]([F:17])=[C:12]([F:14])[F:15])[C:3]([O:5][CH3:6])=[O:4]

Participants

5

Reactant 2

HCID 807IodineHCID 20264408HCID 20264408, compound

Product 1

HCID 14203360HCID 14203360, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8150DiglymeSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 10 g crude methyl perfluoro-7,8-dichloro-4-methyl-3,6-dioxaoctanoate, 5 g zinc dust, 50 ml anhydrous diethylene glycol dimethyl ether and 0.1 g iodine was heated to 140° C., and then distilled. The distillate was washed with water and the product chromatographed to yield appreciable amounts of CF2 =CFOCF2CF(CF3)OCF2COOCH3. The structure of the final product was proven by IR spectroscopy and by conversion with bromine to CF2BrCFBrOCF2CF(CF3)OCF2COOCH3. The structure of the vinyl ether was further confirmed by its boiling point, 75° C. at 50 mm of Hg, and its NMR spectrum.

Workup

  1. distillationdistilled
  2. washThe distillate was washed with water
  3. customthe product chromatographed
  4. customto yield appreciable amounts of CF2 =CFOCF2CF(CF3)OCF2COOCH3

Sources & evidence

ORD record
ord-ec44368390594f2091a20a021043c173
Source dataset
uspto-grants-1985_10
Patent number
US04544458

Reaction notes

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