A convenient synthesis of 3,5-bis(trifluoromethyl)salicylic acid

Article abstract of DOI:10.1080/00397919708007080

A convenient method is reported for the synthesis of the biologically important intermediate, 3,5-bis(trifluoromethyl)-salicylic acid, by a sequence involving diazotization/iodination of 2-bromo-3,5-bis(trifluoromethyl)aniline, displacement of the bromide with sodium methoxide, and carboxylation of the anion generated by lithium-iodine exchange with carbon dioxide. Alternatively, the anion could be carbonylated with dimethylformamide and the resulting aldehyde oxidized with Jones reagent. Demethylation of 3,5-bis(trifluoromethyl)anisic acid with boron tribromide gave the title compound.

Full text of DOI:10.1080/00397919708007080

This article was downloaded by: [Moskow State Univ Bibliote]
On: 20 November 2013, At: 02:28
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954
Registered office: Mortimer House, 37-41 Mortimer Street, London W1T 3JH,
UK
Synthetic Communications: An
International Journal for Rapid
Communication of Synthetic
Organic Chemistry
Publication details, including instructions for
authors and subscription information:
http://www.tandfonline.com/loi/lsyc20
A Convenient Synthesis of 3,5-
bis(Trifluoromethyl)Salicylic
Acid
Zhihua Sui a & Mark J. Macielag a
a The R. W. Johnson Pharmaceutical Research
Institute , 1000 Route 202, P.O. Box 300, Raritan,
New Jersey , 08869
Published online: 22 Aug 2006.
To cite this article: Zhihua Sui & Mark J. Macielag (1997) A Convenient Synthesis of
3,5-bis(Trifluoromethyl)Salicylic Acid, Synthetic Communications: An International
Journal for Rapid Communication of Synthetic Organic Chemistry, 27:20, 3581-3590,
DOI: 10.1080/00397919708007080
To link to this article: http://dx.doi.org/10.1080/00397919708007080
PLEASE SCROLL DOWN FOR ARTICLE
Taylor & Francis makes every effort to ensure the accuracy of all the
information (the “Content”) contained in the publications on our platform.
However, Taylor & Francis, our agents, and our licensors make no
representations or warranties whatsoever as to the accuracy, completeness,
or suitability for any purpose of the Content. Any opinions and views
expressed in this publication are the opinions and views of the authors, and
are not the views of or endorsed by Taylor & Francis. The accuracy of the
Content should not be relied upon and should be independently verified with
primary sources of information. Taylor and Francis shall not be liable for any

losses, actions, claims, proceedings, demands, costs, expenses, damages,
and other liabilities whatsoever or howsoever caused arising directly or
indirectly in connection with, in relation to or arising out of the use of the
Content.
This article may be used for research, teaching, and private study purposes.
Any substantial or systematic reproduction, redistribution, reselling, loan,
sub-licensing, systematic supply, or distribution in any form to anyone is
expressly forbidden. Terms & Conditions of access and use can be found at
http://www.tandfonline.com/page/terms-and-conditions