Regioselective electrophilic aromatic bromination: theoretical analysis and experimental verification

Hui-Jing Li; Yan-Chao Wu; Jian-Hong Dai; Yan Song; Runjiao Cheng; Yuanyuan Qiao

doi:10.3390/molecules19033401

Regioselective electrophilic aromatic bromination: theoretical analysis and experimental verification

Molecules. 2014 Mar 20;19(3):3401-16. doi: 10.3390/molecules19033401.

Authors

Hui-Jing Li¹, Yan-Chao Wu², Jian-Hong Dai³, Yan Song⁴, Runjiao Cheng⁵, Yuanyuan Qiao⁵

Affiliations

¹ School of Marine Science and Technology, Harbin Institute of Technology at Weihai, Weihai 264209, China.
² School of Marine Science and Technology, Harbin Institute of Technology at Weihai, Weihai 264209, China. ycwu@iccas.ac.cn.
³ School of Materials Science and Engineering, Harbin Institute of Technology at Weihai, Weihai 264209, China.
⁴ School of Materials Science and Engineering, Harbin Institute of Technology at Weihai, Weihai 264209, China. sy@hitwh.edu.cn.
⁵ Central Laboratory, College of Chemistry, and Computational Center for Molecular Science, Nankai University, Tianjin 300071, China.

Abstract

Electrophilic aromatic bromination is the most common synthetic method used to prepare aryl bromides, which are very useful intermediates in organic synthesis. To understand the experimental results in electrophilic aromatic brominations, ab initio calculations are used here for a tentative analysis of the positional selectivity. The calculated results agree well with the corresponding experimental data, and the reliability of the resulting positional selectivity was verified by the corresponding experimental data.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Bromides / chemistry*
Halogenation*
Models, Chemical*
Models, Molecular

Substances

Bromides