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 Process for the preparation of 1-bromoethyl hydrocarbonyl carbonates and new 1-bromoethyl hydrocarbonyl carbonates

Details
Inventors: Malfroot, Thierry; Piteau, Marc; Senet, Jean-Pierre;
Assignee: Societe Nationale des Poudres et Explosifs (Paris, FR)
Primary Examiner: Shippen; Michael L.
Assistant Examiner:
Attorney, Agent or Firm: Bucknam and Archer

The invention relates to a process for the preparation of 1-bromoethyl hydrocarbonyl carbonates, characterized in that anhydrous hydrobromic acid is reacted with a vinyl hydrocarbonyl carbonate of formula ##STR1## in which R denotes a saturated, substituted or unsubstituted C.sub.1 -C.sub.12 aliphatic radical or C.sub.5 -C.sub.24 alicyclic radical, or a substituted or unsubstituted aromatic radical, at a temperature between 10.degree. and 100.degree. C. The invention also relates to the new 1-bromoethyl hydrocarbonyl carbonates of formula: ##STR2## These carbonates are particularly sought after for introducing a carbonate group into a molecule.

DETAILED DESCRIPTION We claim: 1.
A process for the preparation of a 1-bromoethyl hydrocarbonyl carbonate, which consists of reacting anhydrous hydrobromic acid with a vinyl hydrocarbonyl carbonate of formula ##STR14## wherein R is a saturated, C.
sub.
1 -C.
sub.
8 aliphatic radical or alicyclic radical or an aromatic radical, wherein said aliphatic, alicyclic or aromatic radical is unsubstituted or substituted by halogen atoms or saturated hydrocarbon radicals, at a temperature between 10.
degree.
C.
and 100.
degree.
C.
and isolating said 1-bromoethyl hydrocarbonyl carbonate from the reaction mixture.
2.
The process for the preparation of a 1-bromoethyl hydrocarbonyl carbonate of formula ##STR15## wherein R.
sup.
1 is ethyl, isopropyl, n-octyl or phenyl, which consists of reacting anhydrous hydrobromic acid with a vinyl hydrocarbonyl carbonate of formula ##STR16## wherein R.
sup.
1 is as defined hereinabove at a temperature between 10.
degree.
C.
and 100.
degree.
C.
and isolating said 1-bromoethyl hydrocarbonyl carbonate from the reaction mixture.
3.
The process according to claim 1, wherein gaseous hydrobromic acid is slowly introduced into the reaction medium.
4.
The process according to claim 1, wherein hydrobromic acid is added in a quantity of between 1.
05 and 1.
4 equivalents per equivalent of vinyl carbonate.
5.
The process according to claim 1, wherein the reaction is carried out in the absence of solvent.
6.
The process according to claim 5, wherein the reaction temperature is between 15.
degree.
and 60.
degree.
C.




Description:
The invention relates to a new process for the preparation of 1-bromoethyl hydrocarbonyl carbonates.
The invention also relates to new 1-bromoethyl hydrocarbonyl carbonates.
While some alpha-bromo carbonates are mentioned in a small number of publications, only 1-bromoethyl ethyl carbonate appears to have been the subject of an accurate description.
Its preparation does not appear to be easy.
Various preparative processes have been suggested.
One of these consists in reacting a 1-bormoethyl haloformate with ethanol, according to the reaction: ##STR3## where X denotes chlorine or bromine



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