Chlorination of 2,5-DMA?

[KidCurry]

Would it be possible to chlorinate 2,5-dimethoxyamphetamine (t o yield DOC) with HCl in tert-butyl hydroperoxide as discussed in the following document:

https://www.thevespiary.org/rhodium/Rhodium/chemistry/halosuccinimide.txt

?

I've searched all day, and the alternatives doesn't look that hot, rather avoid liquid chlorine and perchloric acid (NCS-route seemed like a simple procedure otherwise) if I could.

[Barium]

How 'bout UTFSE a bit and look for the alternatives used to make 2C-C (the direct homolog of DOC). I posted something about just that about a year ago. It can't get much easier really.

[Rhodium]

You posted about the Oxone/KCl procedure a while ago:

Post 384324

(Barium: "A little 2C-C perhaps", Novel Discourse)

Did you ever boost your yields?

[Barium]

I lost interest in that family once I successfully made them.  
No oxone halogenation has been performed since that one. If I ever go back to them again I am more interested in making them without having to go through 2C-H or DMA.
I want challenges, damnit!   

[KidCurry]

Thank you very much!
Just one question, in you're writeup I suppose you forgot to mention the addition of KCl? Just dissolve KCl and 2,5-DMA in H2O/MeOH and then addition of oxone as in the 2C-I writeup?

[GC_MS]

I have never been succesful in chlorination or iodination of 2C-H and 2,5-DMA with oxone and KCl (or KI). On the other hand, I have been succesful in using the same method for bromination of anisole.

[Barium]

I did not forget to mention the KCl addition. The chloride source was the 2C-H*HCl. It acts as amine source and chloride source at the same time.