Synthesis of alpha-monobrominated pyrrole derivatives

L. Groenendaal; M.E. Loo, van; J.A.J.M. Vekemans; E.W. Meijer

doi:10.1080/00397919508011772

Synthesis of alpha-monobrominated pyrrole derivatives

L. Groenendaal
, M.E. Loo, van
, J.A.J.M. Vekemans
, E.W. Meijer

Research output: Contribution to journal › Article › Academic › peer-review

18 Citations (Scopus)

170 Downloads (Pure)

Abstract

Surprisingly stable N-t-BOC-2-bromo-4-hexyl-pyrrole is prepared from N-t-BOC-2-trimethylstannyl-4-hexyl-pyrrole using N-bromosuccinimide as reagent. The bromo-stannyl exchange reaction is performed quantitatively in THF at -70[ddot]C under inert atmosphere. Similarly, N-t-BOC-2-bromopyrrole and N-benzenesulfonyl-2-bromopyrrole have been synthesized from N-t-BOC-2-trimethylstannylpyrrole and N-benzenesulfonyl-2-trimethylstannylpyrrole, respectively.

Original language	English
Pages (from-to)	1589-1600
Number of pages	12
Journal	Synthetic Communications
Volume	25
Issue number	10
DOIs	https://doi.org/10.1080/00397919508011772
Publication status	Published - 1995

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title = "Synthesis of alpha-monobrominated pyrrole derivatives",

abstract = "Surprisingly stable N-t-BOC-2-bromo-4-hexyl-pyrrole is prepared from N-t-BOC-2-trimethylstannyl-4-hexyl-pyrrole using N-bromosuccinimide as reagent. The bromo-stannyl exchange reaction is performed quantitatively in THF at -70[ddot]C under inert atmosphere. Similarly, N-t-BOC-2-bromopyrrole and N-benzenesulfonyl-2-bromopyrrole have been synthesized from N-t-BOC-2-trimethylstannylpyrrole and N-benzenesulfonyl-2-trimethylstannylpyrrole, respectively.",

author = "L. Groenendaal and \{Loo, van\}, M.E. and J.A.J.M. Vekemans and E.W. Meijer",

year = "1995",

doi = "10.1080/00397919508011772",

language = "English",

volume = "25",

pages = "1589--1600",

journal = "Synthetic Communications",

issn = "0039-7911",

publisher = "Taylor and Francis Ltd.",

number = "10",

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TY - JOUR

T1 - Synthesis of alpha-monobrominated pyrrole derivatives

AU - Groenendaal, L.

AU - Loo, van, M.E.

AU - Vekemans, J.A.J.M.

AU - Meijer, E.W.

PY - 1995

Y1 - 1995

N2 - Surprisingly stable N-t-BOC-2-bromo-4-hexyl-pyrrole is prepared from N-t-BOC-2-trimethylstannyl-4-hexyl-pyrrole using N-bromosuccinimide as reagent. The bromo-stannyl exchange reaction is performed quantitatively in THF at -70[ddot]C under inert atmosphere. Similarly, N-t-BOC-2-bromopyrrole and N-benzenesulfonyl-2-bromopyrrole have been synthesized from N-t-BOC-2-trimethylstannylpyrrole and N-benzenesulfonyl-2-trimethylstannylpyrrole, respectively.

AB - Surprisingly stable N-t-BOC-2-bromo-4-hexyl-pyrrole is prepared from N-t-BOC-2-trimethylstannyl-4-hexyl-pyrrole using N-bromosuccinimide as reagent. The bromo-stannyl exchange reaction is performed quantitatively in THF at -70[ddot]C under inert atmosphere. Similarly, N-t-BOC-2-bromopyrrole and N-benzenesulfonyl-2-bromopyrrole have been synthesized from N-t-BOC-2-trimethylstannylpyrrole and N-benzenesulfonyl-2-trimethylstannylpyrrole, respectively.

U2 - 10.1080/00397919508011772

DO - 10.1080/00397919508011772

M3 - Article

SN - 0039-7911

VL - 25

SP - 1589

EP - 1600

JO - Synthetic Communications

JF - Synthetic Communications

IS - 10

ER -

Synthesis of alpha-monobrominated pyrrole derivatives

Abstract

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