Dichloromethane → (2-Fluoro-2,2-dinitroethoxy)ethene

HRID 2295904Notes

Reaction equation

HRID 2295904 reaction equation
C(Cl)Cl.[CH:4](OC=C)=[CH2:5].[F:9][C:10]([N+:16]([O-:18])=[O:17])([N+:13]([O-:15])=[O:14])[CH2:11][OH:12].FC(F)(F)C(O)=O>C(Cl)(Cl)(Cl)Cl.O>[CH:4]([O:12][CH2:11][C:10]([F:9])([N+:16]([O-:18])=[O:17])[N+:13]([O-:15])=[O:14])=[CH2:5]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 8024Vinyl etherHCID 28189Ethanol, 2-fluoro-2,2-dinitro-

Product 1

HCID 12385929(2-Fluoro-2,2-dinitroethoxy)etheneYield 73.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

A 50 ml single necked, round bottom flask was charged with 20 ml of methylene chloride, 0.5 g (7.14 mmoles) divinyl ether (I), 1.1 g (7.14 mmoles) 2-fluoro-2,2-dinitroethanol, and 0.1 g red mercuric oxide. The solution was stirred with a Teflon coated magnetic bar while 100 μl trifluoroacetic acid was used. The reaction flask was then fitted with a water cooled reflux condenser and drying tube filled with Drierite desiccant. The reaction mixture was then stirred under reflux (~37° C.) for 22.5 hours. At the end of this period, the methylene chloride solvent was removed in vacuo, leaving a slightly yellow, clear oil. The oil was taken up in carbon tetrachloride and eluted with 35 ml carbon tetrachloride through 2.5 g neutral alumina (pH 7.3) packed in a 15 ml "course" glass sintered funnel. The carbon tetrachloride was removed in vacuo, leaving 0.94 g of colorless crude 2-fluoro-2,2-dinitroethyl vinyl ether (VII) which was shown by nuclear magnetic resonance spectrometry to be 84 percent pure.

Workup

  1. temperaturecooled
  2. temperaturereflux condenser
  3. customdrying tube
  4. additionfilled with Drierite desiccant
  5. temperatureunder reflux (~37° C.) for 22.5 hours
  6. customAt the end of this period, the methylene chloride solvent was removed in vacuo
  7. customleaving a slightly yellow, clear oil
  8. washeluted with 35 ml carbon tetrachloride through 2.5 g neutral alumina (pH 7.3)
  9. customThe carbon tetrachloride was removed in vacuo

Sources & evidence

ORD record
ord-da5b3fb719904538884b59b5cfc510ee
Source dataset
uspto-grants-1984_01
Patent number
US04426540

Reaction notes

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