69298-57-3

Usage

InChI:InChI=1/C3H4Br2O/c4-1-3(5)2-6/h1,6H,2H2

Upstream product

• 107-19-7 propargyl alcohol 
• 69298-56-2 (E)-2,3-dibromoprop-2-en-1-ol 

Relevant academic research and scientific papers

Synthesis of Exo- and Endocyclic Enamides Through Copper-Catalyzed Regioselective Intramolecular N-Halovinylation

Cross-couplings between amides and 1,2-dihaloalkenes are an efficient and straightforward way to access β-haloenamides which, in turn, can be functionalized into complex, stereodefined enamide motifs. However, the intramolecular version of these cross-couplings, leading to cyclic β-haloenamides, has not been formally studied. In this paper, we report an investigation of factors affecting the efficiency of the reaction and its selectivity between potential exo and endo cyclization products. We demonstrate that exo/endo selectivity is largely determined by ring strain, whether it arises from the size of the resulting ring or from the structure of the starting compound, but that selectivity can also be modulated by varying reaction conditions. Finally, we show that resulting β-haloenamides readily undergo transition metal-catalyzed reactions, making this sequence a viable way to access highly functionalized cyclic enamides.

A domino copper-catalyzed C-N and C-O cross-coupling for the conversion of primary amides into oxazoles

A variety of oxazoles can efficiently be prepared, in a single step and in good yield, from primary amides and 1,2-dihaloalkenes using copper-catalysis. This new method allows the regioselective formation of a range of substituted oxazoles. The required 1,2-dihaloalkenes can prepared by simple treatment of alkynes with elemental bromine or iodine. Georg Thieme Verlag Stuttgart.

BROMINATION OF ALKENES AND ALKYNES WITH BIS(DIMETHYLACETAMIDO)HYDROGEN TRIBROMIDE

The brominating characteristics of bis(dimethylacetamido)hydrogen tribromide were studied in the bromination of a series of alkenes and alkynes. The yields of the bromination products are the same as with molecular bromine and are noticeably higher in the case of the most reactive alkenes.

Halogenated esters of phosphorus-containing acids (III)

This invention deals with new phosphorus-containing esters having the formula STR1 wherein R represents a divalent hydrocarbon radical containing 1-20 carbon atoms; R' represents X, hydrogen or R"; R" represents a monovalent hydrocarbon radical containing 1-20 carbon atoms; and X represents chlorine or bromine. These new esters are useful particularly as fire retardants, agricultural chemicals, fuel additives, plasticizers, monomers and intermediates for the synthesis of other useful derivatives.

Unsaturated ester-amides of halogenated alkenes

This invention deals with new unsaturated ester-amides of α,β-unsaturated polycarboxylic acids derived from halogenated alcohols of the formula EQU1 wherein R is a divalent hydrocarbon moiety having at least one and no more than 10 carbon atoms, X is a member selected from the class of bromine and chlorine, and R' is a member selected from the class of hydrogen and a monovalent hydrocarbon containing at least one and no more than 20 carbon atoms. Typical ester-amides are the maleates, fumarates, itaconates and citraconates. These monomers possess fire-retardant properties and are useful for the synthesis of polymers and copolymers.