Propose a synthesis of p-bromotoluene, Chemistry

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Usually we grudgingly accept that syntheses involving activated EAS reactions will unavoidably yield both ortho and para isomers, and this inefficiency is acceptable in exam and homework syntheses unless otherwise indicated. However, it is possible to design reaction sequences to minimize such unwanted side-products. Propose a 5-6 step synthesis of p-bromotoluene from benzene that minimizes production of the ortho regioisomer.


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