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 $$\ce{PCl5}$$.