How do we know whether we will get a mono substituted or tri-substituted product during electrophilic aromatic substitution?
It is like others have already noted that phenol is very strongly ortho-para directing, while bromine is only slightly deactivating (or sometimes slightly activating). It is so activating that you do not even need a Lewis acidic catalyst or elevated temperature to let the reaction go fast and in good yield. Moreover, if you want the mono substituted product you will actually need to cool the reaction down to &lt; 5 °C and use the rather dangerously flammable solvent $\ce{CS_2}$, yielding 4-bromophenol in 85% yield (source: Vogel). I assume the para product is formed due to the fact that there is no significant difference in electron density between ortho and para carbon atom while ortho is slightly sterically hindered.