From: Chapman, Robert D (ChapmanRD$##$navair.navy.mil)
Date: Wed Jun 14 2000 - 12:33:18 EDT
A.H. Jackson, in R.A. Jones, "Pyrroles: Part One," says: "Thus, bromination
of 1-benzylpyrrole at 0 C, under conditions in which the hydrogen bromide
produced by the reaction is continuously removed, afforded
1-benzyl-3-bromopyrrole as the main component (55%), with none of the
2-bromo derivative" [Anderson, H.J.; Griffiths, S.J. Can. J. Chem. 1967, 45,
2227].
Robert D. Chapman, Ph.D.
Chemistry & Materials Division (Code 4T4200D)
Naval Air Warfare Center
China Lake, CA 93555 USA
> ----------
> From: Gianluca Sbardella
> Sent: June 14, 2000 1:14 AM
> To: Multiple recipients of list orglist
> Subject: ORGLIST: 3-bromination of N-substituted pyrroles
>
> Dear Colleagues,
> first of all my apologies for any crossposting.
> I recently planned to synthesize some 3-phenyl-N-substituted pyrroles
> via Suzuki coupling of (substituted)benzene boronic acids with the
> proper 3-bromo-pyrroles. Alas, the only method of 3-bromination of
> pyrroles I found was an isomerization in a trifluoroacetic acid medium
> of 2-bromo derivatives. Does anybody ever had any experence on this kind
>
> of reaction?
> Thank you very much in advance.
> If the topic could be interesting for any other I will summarize to the
> list.
> Sincerely,
>
> Dr. Gianluca Sbardella, Ph.D.
> Diprtimento di Studi Farmaceutici
> Universita' degli studi di Roma "La Sapienza"
> Rome - Italy
>
> __________________
>
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