2-(3-Bromo-4-meth­oxy­phen­yl)acetic acid

The title compound C(9)H(9)BrO(3), was synthesized by the regioselective bromination of 4-meth­oxy­phenyl­acetic acid using bromine in acetic acid in a 84% yield. In the mol­ecular structure, the meth­oxy group is almost coplanar with the phenyl ring within 0.06 Å; the acetic acid substituent is til...

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Detalles Bibliográficos
Autores principales: Guzei, Ilia A., Gunderson, Alan R., Hill, Nicholas J.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3007027/
https://www.ncbi.nlm.nih.gov/pubmed/21587800
http://dx.doi.org/10.1107/S1600536810020143
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author Guzei, Ilia A.
Gunderson, Alan R.
Hill, Nicholas J.
author_facet Guzei, Ilia A.
Gunderson, Alan R.
Hill, Nicholas J.
author_sort Guzei, Ilia A.
collection PubMed
description The title compound C(9)H(9)BrO(3), was synthesized by the regioselective bromination of 4-meth­oxy­phenyl­acetic acid using bromine in acetic acid in a 84% yield. In the mol­ecular structure, the meth­oxy group is almost coplanar with the phenyl ring within 0.06 Å; the acetic acid substituent is tilted by 78.15 (7)° relative to the ring. The C—C—C angles at the OMe, acetyl and Br substituents are 118.2 (2), 118.4 (2) and 121.5 (2)°, respectively, indicating that the Br atom is electron-withdrawing, whereas the other substituents possess electron-donating properties. In the crystal, the mol­ecules form centrosymmetric strongly O—H⋯O hydrogen-bonded dimers of the type R (2) (2)(8).
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spelling pubmed-30070272010-12-30 2-(3-Bromo-4-meth­oxy­phen­yl)acetic acid Guzei, Ilia A. Gunderson, Alan R. Hill, Nicholas J. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound C(9)H(9)BrO(3), was synthesized by the regioselective bromination of 4-meth­oxy­phenyl­acetic acid using bromine in acetic acid in a 84% yield. In the mol­ecular structure, the meth­oxy group is almost coplanar with the phenyl ring within 0.06 Å; the acetic acid substituent is tilted by 78.15 (7)° relative to the ring. The C—C—C angles at the OMe, acetyl and Br substituents are 118.2 (2), 118.4 (2) and 121.5 (2)°, respectively, indicating that the Br atom is electron-withdrawing, whereas the other substituents possess electron-donating properties. In the crystal, the mol­ecules form centrosymmetric strongly O—H⋯O hydrogen-bonded dimers of the type R (2) (2)(8). International Union of Crystallography 2010-06-05 /pmc/articles/PMC3007027/ /pubmed/21587800 http://dx.doi.org/10.1107/S1600536810020143 Text en © Guzei et al. 2010 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Guzei, Ilia A.
Gunderson, Alan R.
Hill, Nicholas J.
2-(3-Bromo-4-meth­oxy­phen­yl)acetic acid
title 2-(3-Bromo-4-meth­oxy­phen­yl)acetic acid
title_full 2-(3-Bromo-4-meth­oxy­phen­yl)acetic acid
title_fullStr 2-(3-Bromo-4-meth­oxy­phen­yl)acetic acid
title_full_unstemmed 2-(3-Bromo-4-meth­oxy­phen­yl)acetic acid
title_short 2-(3-Bromo-4-meth­oxy­phen­yl)acetic acid
title_sort 2-(3-bromo-4-meth­oxy­phen­yl)acetic acid
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3007027/
https://www.ncbi.nlm.nih.gov/pubmed/21587800
http://dx.doi.org/10.1107/S1600536810020143
work_keys_str_mv AT guzeiiliaa 23bromo4methoxyphenylaceticacid
AT gundersonalanr 23bromo4methoxyphenylaceticacid
AT hillnicholasj 23bromo4methoxyphenylaceticacid

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