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I got this question from an o-chem II exam which kinda puzzles me a bitquestion

My proposed path is: enter image description here

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

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    $\begingroup$ Why do you think this is not correct? It is a bit old-tech but it will work. It is possible to directly fluorinate toluene, but you get a mixture of o and p ncbi.nlm.nih.gov/pmc/articles/PMC8329385 $\endgroup$
    – Waylander
    Jan 15, 2023 at 12:16
  • $\begingroup$ I am wondering that bromine reacts specifically with methyl, but my organic chemistry is very rusty. $\endgroup$
    – Poutnik
    Jan 15, 2023 at 12:33
  • $\begingroup$ @Poutnik under radical conditions it will $\endgroup$
    – Waylander
    Jan 15, 2023 at 12:47
  • $\begingroup$ @Waylander I was being skeptical about the last step (bromonation), but seems like it was correct after all, thanks! $\endgroup$
    – frostbite
    Jan 15, 2023 at 12:51
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    $\begingroup$ To complement a search in a reaction/literature database like Reaxys/Scifinder, there is an entry p-Fluorobenzotribromide with entries in sections literature and patents. Beside reference to the patent, double click on title of the patent reviews the patent (example) including section 7 / linked molecules (example). Although a search by patent can take long/be in part inaccessible by language/script. $\endgroup$
    – Buttonwood
    Jan 15, 2023 at 14:01

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This route will work.

p-Nitrotoluene is the major product of toluene nitration and may be isolated by distillation and recrystallisation, procedure here

This recent paper describes low temperature and light catalysed Balz-Schiemann conditions which are rather more user-friendly than some of the older procedures.

This patent describes a method of brominating the p-F-toluene to the benzotrifluoride

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