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Chemistry - Anti-Markovnikov addition of HCl

One way to do it would be do first do a hydroboration-oxidation reaction, which leads to the anti-Markovnikov addition of $\ce{H2O}$. So you will get an $\ce{-OH}$ group instead of $\ce{-Cl}$. Then, we can replace the $\ce{-OH}$ group with $\ce{-Cl}$ by treating it with $\ce{PCl3}$ or $\ce{PCl5}$.

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