Grubbs II catalyst mediated ring-closing metathesis (RCM) of mono-brominated dienes is reported to proceed in moderate to good yields (40–80%) where the linking chain contains five atoms, leading to carbocyclic and heterocyclic 7-membered bromo-olefins. Notably, RCM to form 5-, 6- or 8-membered bromo-olefins was unsuccessful, with the exception of one example where RCM afforded diethyl 3-bromocyclohex-3-ene-1,1-dicarboxylate. In this case a bromomethyl-substituted cyclohexene was obtained as a byproduct. The utility of selected bromo-olefin RCM products was demonstrated through their participation in Suzuki-Miyaura reactions. Vinyl halide exchange (BrCl) was noted as a side reaction under RCM conditions.