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Starting with benzene, design a synthesis of m-bromoethylbenzene



Solution:

Bromine is ortho/para directing and ethyl is ortho/para directing as well. However, the groups are meta to one another. We need to do Friedel Crafts Acylation first to add an acyl group which is meta directing. We then add Br. Finally, we remove the double bond O from the acyl group via Clemmenson or Wolff Kischner reduction to turn it into the ethyl group.

Starting with benzene, design a synthesis of m-bromoethylbenzene
Starting with benzene, design a synthesis of m-bromoethylbenzene

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