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How to convert benzene to 2-nitrostyrene as the major product?

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I actually came up with a conversion but I don't know if it's correct or not:

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  • $\begingroup$ Since nitro is a ring deactivator, I think we can use $\ce{CH2=CH-Cl + AlCl3}$ to create a polymer. I am not sure though $\endgroup$ – dr.drizzy Mar 3 '18 at 17:18
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  1. Brominate to form bromobenzene

  2. Nitrate and separate by column chromatography to isolate o-nitrobromobenzene (read)

  3. Vinylate with vinylboroxane/Pd(PPh3)4/K2CO3/DME
    Reference: J.Org. Chem. 67 (2002) 4968, Review JCS Chem. Comm. 2009 20-33

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  • $\begingroup$ Well thanks for the answer...i have never heard of the reaction in the third step....but still...thank you!! $\endgroup$ – Jai Arora Mar 3 '18 at 18:23
  • $\begingroup$ The exact transformation is described in the JoC reference if you can get to it. It appears in a table in the review article with 74% yield. $\endgroup$ – Waylander Mar 3 '18 at 18:30
  • $\begingroup$ Okay... I'll see if i can get to it somehow! Ty! $\endgroup$ – Jai Arora Mar 3 '18 at 18:33

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