Halogenation of alkenes
10 real reactions from the literature, on six-membered cycloalkenes, terminal alkenes, α,β-unsaturated acids and α,β-unsaturated esters. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.
Loading examples…
-
Halogenation of alkene: undecylenic acid (a terminal alkene) with Br2; ether, 0 °C gives 10,11-dibromoundecanoic acid (the vicinal dihalide).
-
Halogenation of alkene: fumaric acid (an α,β-unsaturated acid) with Br2, H2O; Δ gives 2,3-dibromosuccinic acid (the vicinal dihalide).
-
Halogenation of alkene: cyclohexene (a six-membered cycloalkene) with Br2, CH3CH2OH; CCl4; −5 to −1 °C gives 1,2-dibromocyclohexane (the vicinal dihalide).
-
Halogenation of alkene: ethyl cinnamate (an α,β-unsaturated ester) with Br2; CCl4, 0 °C gives ethyl 2,3-dibromo-3-phenylpropanoate (the vicinal dihalide).
-
Halogenation of alkene: a trisubstituted six-membered cycloalkene with Br2, NaOAc; AcOH, ether gives the vicinal dihalide.
-
Halogenation of alkene: benzylideneacetone (an α,β-unsaturated ketone) with Br2, CCl4; dark gives 3,4-dibromo-4-phenyl-2-butanone (the vicinal dihalide).
-
Halogenation of alkene: oleic acid (a cis-1,2-disubstituted alkene) with Br2; ether gives the vicinal dihalide.
-
Halogenation of alkene: (3aR,7aS)-1,3,3a,4,7,7a-hexahydro-2-benzofuran (a six-membered cycloalkene) with (±) gives the vicinal dihalide.
-
Halogenation of alkene: (E)-oct-4-ene (a trans-1,2-disubstituted alkene) with (±) gives the vicinal dihalide.
-
Halogenation of alkene: 1,3-butadiene (a conjugated diene) with 100% gives trans-1,4-dibromo-2-butene (the dihalide).