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

Participants

Reaction Steps

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.

Provenance & Evidence