Regioselective bromination of 1,4-dimethoxy-2,3-dimethylbenzene and conversion into sulfur-functionalised benzoquinones

Robert Alan Aitken; Siddharth Janak Jethwa; Neville Vincent Richardson; Alexandra Martha Zoya Slawin

doi:10.1016/j.tetlet.2016.02.091

Regioselective bromination of 1,4-dimethoxy-2,3-dimethylbenzene and conversion into sulfur-functionalised benzoquinones

Robert Alan Aitken, Siddharth Janak Jethwa, Neville Vincent Richardson, Alexandra Martha Zoya Slawin

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

Abstract

The NBS bromination of 1,4-dimethoxy-2,3-dimethylbenzene has been examined under a variety of conditions in both 1,1,1-trichloroethane and benzotrifluoride. Four different bromination products have been isolated including the previously unknown 1-bromo-4-bromomethyl-2,5-dimethoxy-3-methylbenzene whose single crystal X-ray structure is presented. The synthetically useful 2,3-bis(bromomethyl)-1,4-dimethoxybenzene is readily prepared using either solvent and it has been converted into new sulfur-containing quinone derivatives

Original language	English
Pages (from-to)	1563-1566
Number of pages	4
Journal	Tetrahedron Letters
Volume	57
Issue number	14
Early online date	27 Feb 2016
DOIs	https://doi.org/10.1016/j.tetlet.2016.02.091
Publication status	Published - 11 Mar 2016

Keywords

Bromination
Benzotrifluoride
Solvent effects
X-ray structures

Access to Document

10.1016/j.tetlet.2016.02.091

Aitken_2016_TL_Regioselective_AAM
Copyright © 2016 Elsevier Ltd. All rights reserved. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://dx.doi.org/10.1016/j.tetlet.2016.02.091
Accepted author manuscript, 287 KB

Handle.net

Persistent link

Cite this

@article{2f962e809d5f40ea86552be217adc2b2,

title = "Regioselective bromination of 1,4-dimethoxy-2,3-dimethylbenzene and conversion into sulfur-functionalised benzoquinones",

abstract = "The NBS bromination of 1,4-dimethoxy-2,3-dimethylbenzene has been examined under a variety of conditions in both 1,1,1-trichloroethane and benzotrifluoride. Four different bromination products have been isolated including the previously unknown 1-bromo-4-bromomethyl-2,5-dimethoxy-3-methylbenzene whose single crystal X-ray structure is presented. The synthetically useful 2,3-bis(bromomethyl)-1,4-dimethoxybenzene is readily prepared using either solvent and it has been converted into new sulfur-containing quinone derivatives",

keywords = "Bromination, Benzotrifluoride, Solvent effects, X-ray structures",

author = "Aitken, \{Robert Alan\} and Jethwa, \{Siddharth Janak\} and Richardson, \{Neville Vincent\} and Slawin, \{Alexandra Martha Zoya\}",

year = "2016",

month = mar,

day = "11",

doi = "10.1016/j.tetlet.2016.02.091",

language = "English",

volume = "57",

pages = "1563--1566",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier",

number = "14",

}

TY - JOUR

T1 - Regioselective bromination of 1,4-dimethoxy-2,3-dimethylbenzene and conversion into sulfur-functionalised benzoquinones

AU - Aitken, Robert Alan

AU - Jethwa, Siddharth Janak

AU - Richardson, Neville Vincent

AU - Slawin, Alexandra Martha Zoya

PY - 2016/3/11

Y1 - 2016/3/11

N2 - The NBS bromination of 1,4-dimethoxy-2,3-dimethylbenzene has been examined under a variety of conditions in both 1,1,1-trichloroethane and benzotrifluoride. Four different bromination products have been isolated including the previously unknown 1-bromo-4-bromomethyl-2,5-dimethoxy-3-methylbenzene whose single crystal X-ray structure is presented. The synthetically useful 2,3-bis(bromomethyl)-1,4-dimethoxybenzene is readily prepared using either solvent and it has been converted into new sulfur-containing quinone derivatives

AB - The NBS bromination of 1,4-dimethoxy-2,3-dimethylbenzene has been examined under a variety of conditions in both 1,1,1-trichloroethane and benzotrifluoride. Four different bromination products have been isolated including the previously unknown 1-bromo-4-bromomethyl-2,5-dimethoxy-3-methylbenzene whose single crystal X-ray structure is presented. The synthetically useful 2,3-bis(bromomethyl)-1,4-dimethoxybenzene is readily prepared using either solvent and it has been converted into new sulfur-containing quinone derivatives

KW - Bromination

KW - Benzotrifluoride

KW - Solvent effects

KW - X-ray structures

UR - http://www.sciencedirect.com/science/article/pii/S0040403916302003#appd002

UR - https://www.scopus.com/pages/publications/85030259503

U2 - 10.1016/j.tetlet.2016.02.091

DO - 10.1016/j.tetlet.2016.02.091

M3 - Article

SN - 0040-4039

VL - 57

SP - 1563

EP - 1566

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 14

ER -

Regioselective bromination of 1,4-dimethoxy-2,3-dimethylbenzene and conversion into sulfur-functionalised benzoquinones

Abstract

Keywords

Access to Document

Handle.net

Other files and links

Fingerprint