Product of reaction between cyclohexene and bromine in methanol at 273 K

What product could we expect when we let cyclohexene react with an equivalent of bromine in methanol at 0 °C? Is it just the trans-addition of bromine (rac.) or also the SN1-susbtitution on a carbon due to MeO? Maybe twice? See below:


[![reaction between cyclohexene and bromine in methanol](https://i.stack.imgur.com/IkBBJ.png)](https://i.stack.imgur.com/IkBBJ.png)




It starts with the formation of brominium ion, as in direct bromination of alkenes. If you do not know the mechanism, you can refer to it [here, at MasterOrganicChemistry](https://www.masterorganicchemistry.com/2013/03/15/alkene-bromination-mechanism/).


[![enter image description here](https://i.stack.imgur.com/bbA84.png)](https://i.stack.imgur.com/bbA84.png)


But here, the $\ce{MeOH}$ can itself act as a potential nucleophile. It is similar to if $\ce{H2O}$ is used as a solvent - refer the formation of halohydrin [here](https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_(McMurry)/08%3A_Alkenes-_Reactions_and_Synthesis/8.03%3A_Halohydrins_from_Alkenes_-_Addition_of_HOX).


Since $\ce{MeOH}$ is available in larger concentrations, it more readily attacks the carbon. Markovnikov rule is followed for determining which carbon is attacked, but in this case, both are symmetrical.


The attack proceeds through $\mathrm{S\_N2}$ mechanism, forming two enantiomers. After the $\ce{C-O}$ bond is formed, the $\ce{MeOH}$ loses $\ce{H+}$ to form ether and $\ce{HBr}$.


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