Bromoaniline, synthesis from benzene

Devise a synthesis of w-bromoaniline starting from benzene. 

Sample Problem 18.8 Design a synthesis of m-bromoaniline from benzene. 

In 1991, Yamanaka and co-workers reported the synthesis of indoles from 2-bromoanilines and (Z)-l-etho qr-2-tributylstannylethene in a two-step manner. Indoles were formed in low yields by treating the Stille eoupling product with TsOH in benzene. lFf-Isoehromen-1-ones can be produeed by adding 6 N HCl to the Stille eoupling produet with 2-bromobenzoates as substrates. 

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