Bromobenzene (${\mathrm{C}}_6{\mathrm{H}}_5\mathrm{Br}$)

${\mathrm{C}}_6{\mathrm{H}}_5\mathrm{Br}$, an aryl bromide that can be converted to an aryl grignard reagent. Bromine directs electrophilic aromatic substitution preferentially to the ortho and para positions while deactivating the ring overall.