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DISCLAIMER: I am not using any of this information to commit a crime, my university has a license from the relevant authorities to investigate clandestine chemical procedures.

We are investigating an amateur conversion eugenol to the 4-(2-bromopropyl)catechol compound you see there. In theory concentrated hydrogen bromide should be able to cleave the ether, yielding methyl bromide, which can be easily removed from the system, and also add to the double bond in markovnikov fashion. I have some questions for how this reaction can be performed. First of all, what solvent should be used? I am thinking of using acetic acid but i am slightly worried about acetate as a competing nucleophile, especially considering that eugenol acetate (alcohol replaced with acetic ester) is a naturally occurring component of clove oil meaning it must be somewhat stable. Perhaps I would need to take my impure product containing acetate derivatives and treat it again with HBr to fix it a little bit? Also, at what temperature should this reaction be performed? Please help answer me so we can stop the illicit drug trade.

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    $\begingroup$ You could provide your actual affiliation but you choose to remain anonymous, which makes bringing up the fact that what you are proposing could be used illicitly all the more curious. This is off topic for this site, but since you bring it up, how exactly is sharing this information with you and the wider world going to help stop illicit drug trade? $\endgroup$
    – Buck Thorn
    Sep 13, 2023 at 7:17
  • $\begingroup$ chemistry.meta.stackexchange.com/questions/3619/… $\endgroup$
    – Buck Thorn
    Sep 13, 2023 at 7:21
  • $\begingroup$ Can you provide more context on this? Like, why you need this information and how this info will help you stop illicit drug trade, what is your action on this? $\endgroup$ Sep 13, 2023 at 7:40
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    $\begingroup$ This suspicious question seems to me rather as an attempt to promote drug trade wrapped in a coat pretending the opposite. Any illegal lab worker could write it like this, if he stumbles upon some particular difficult synthesis step. $\endgroup$
    – Poutnik
    Sep 13, 2023 at 16:22
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    $\begingroup$ I’m voting to close this question because it raises suspicious flags and the OP does not address it. $\endgroup$
    – Poutnik
    Sep 13, 2023 at 18:56

1 Answer 1

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Consulting the oracle of wisdom that is Greene's "Protective Groups in Organic Synthesis" produces this reference that describes the cleavage of dialkyl and aryl alkyl ethers with 47% aq HBr at 115C in the presence of phase-transfer catalysts with yields >90%. These conditions would appear to meet your requirements.

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