Bromine → HCID 19915369, compound

Participants

Reaction Steps

After ester formation, additional reactions, most of which are described above, were utilized to further modify the esters themselves. For example, 9,10-dibromo-10,10-difluorodecyl benzoate (XXVI) was prepared by adding elemental bromine to 10,10-difluoro-9 decenyl benzoate (XXV). Subsequently, 9,10-dibromo-10,10-difluorodecyl benzoate was dehydrobrominated using sodium hydride in tetrahydrofuran, yielding 9-bromo-10,10-difluoro-9-decenyl benzoate (XXVII). In order to extend a hydrocarbon chain by three carbon atoms, an unsaturated ester, e.g., 9-decenyl acetate, was reacted with borane-tetrahydrofuran complex and then with acrolein in the presence of hydrochloric acid, producing 13-oxotridecyl acetate (XXIX). As an alternative to catalytic hydrogenolysis to remove a bromine atom, a brominated compound, e.g., 2,4-dibromo-4,4-difluorobutyl acetate (XXXVI), tributyltin hydride, and 1,1'-azobisisobutyronitrile were heated at 120° C., yielding 4-bromo-4,4-difluorobutyl acetate. These reactions are detailed in Examples 12-23.

Provenance & Evidence