Synthesis of a Substituted Indane

From the starting reactants given as the sole carbon source:


[![enter image description here](https://i.stack.imgur.com/VFKz1.png)](https://i.stack.imgur.com/VFKz1.png)


We need to synthesis the following compound (we can use any inorganic reagents).


[![4-(1-bromo-2-methylpropyl)-2,3-dihydro-1H-indene](https://i.stack.imgur.com/o9WtC.png)](https://i.stack.imgur.com/o9WtC.png)


Here is what I tried so far, but I don't think it looks "realistic"


[![enter image description here](https://i.stack.imgur.com/Mwhl9.jpg)](https://i.stack.imgur.com/Mwhl9.jpg)


[![enter image description here](https://i.stack.imgur.com/lL1Cn.jpg)](https://i.stack.imgur.com/lL1Cn.jpg)




I'll be frank about it....you can't get there from here! In @Waylander's words " This is ...a poorly thought out question...". Allow me to pose the question as it should have been asked. How does one synthesize 5-(1-bromo-2-methylpropyl)-2,3-dihydro-1H-indene **1** from benzene, propionic acid, and isobutyric acid?  
  



![](https://i.stack.imgur.com/61dhF.jpg)  
  



Inspection of ketone **2** shows that a Friedel-Crafts acylation of indane **3** does not occur at $\ce{C4}$ but rather at $\ce{C5}$. The synthesis of bromide **1** from ketone **2** requires reduction to a benzylic alcohol (*e. g.*; $\ce{NaBH4/C2H5OH}$) followed by treatment with $\ce{HBr}$. Isobutyric acid and propionic acid are readily converted to their respective acyl chlorides with $\ce{SOCl2}$. As to the preparation of indane from benzene, [this issue has been addressed previously on ChemSE](https://chemistry.stackexchange.com/questions/91606/propose-a-synthesis-of-indane-from-benzene/91753#91753).


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