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First reaction is addition of HBr in presence of peroxide which takes place according to anti-markonikov's rule.
The synthesis of alkyl fluorides is best accomplished by heating an alkyl chloride/bromide in the presence of a metallic fluoride such as AgF, Hg₂F₂, CoF₂ or SbF₃. The reaction is termed as Swarts reaction.
$$H_3C-Br + AgF \longrightarrow H_3C-F + AgBr$$, however this does not effect the bromine directly attached to the benzene ring.
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