How do you synthesize 1-fluoro-4-(tribromomethyl)benzene from toluene

I got this question from an o-chem II exam which kinda puzzles me a bit[![question](https://i.stack.imgur.com/xttFs.png)](https://i.stack.imgur.com/xttFs.png)


My proposed path is:
[![enter image description here](https://i.stack.imgur.com/f6Xaf.png)](https://i.stack.imgur.com/f6Xaf.png)


which doesn't seem to be correct. Is there any other way within the knowledge of o-chem I & II?




This route will work.


p-Nitrotoluene is the major product of toluene nitration and may be isolated by distillation and recrystallisation, procedure [here](https://www.oc-praktikum.de/nop/en/instructions/pdf/1001_en.pdf)


This recent [paper](https://pubs.acs.org/doi/10.1021/acsomega.1c02825) describes low temperature and light catalysed Balz-Schiemann conditions which are rather more user-friendly than some of the older procedures.


This [patent](https://pubchem.ncbi.nlm.nih.gov/patent/EP-0045430-A1) describes a method of brominating the p-F-toluene to the benzotrifluoride


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