Bromine → 1-Bromo-2-(2-bromoethyl)benzene

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Reaction Steps

The four-membered ring of benzocyclobutenes is known to open at elevated temperature to form a very reactive diene which rapidly dimerizes and polymerizes. Molecules containing two or more benzocyclobutene groups are therefore useful as heat-curable thermosetting resins. Also, elastomers or thermoplastics containing benzocyclobutene substituents crosslink on heating. One of the easiest and most useful methods of functionalizing the benzocyclobutene molecule for subsequent production of resins or functionalized polymers is halogenation of the aromatic ring. Bromination with aqueous bromine, for example, can yield 4-bromobenzocyclobutene in over 75% yield. However, a significant proportion of the starting benzocyclobutene (10-15%) reacts with bromine by addition and opening of the four-membered ring to form 1-bromo-2-(2-bromoethyl)benzene.

Provenance & Evidence