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The question is basically to figure about the steps for the following transformation.

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Since ethene is a electron donating group and weakly ortho para directing so it makes electrophilic substitution difficult.hence we must add bromine water($\ce{HOBr}$) to the double bond.After this if we add $\ce{Cl2}/Fe$ we will get ortho and para positions substituted by chlorine.However I am facing difficulty changing the ortho chlorine atoms to iodine.Please suggest me a way to proceed.Thanks.

Pink
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    A vinyl group is electron donating and is weakly ortho-para directing. – ron Jan 04 '17 at 17:19
  • @ron thanks for your comment.I edited the question accordingly. – Pink Jan 05 '17 at 14:49
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    Masking your double bond through addition of one bromine atom is a reasonable first step. Take a look at this earlier answer and consider how sulfonation and the Sandmeyer reaction might prove useful in your synthesis. – ron Jan 05 '17 at 18:40

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