o-Xylylene Bis(Triethyl Ammonium Tribromide) as a Mild and Recyclable Reagent for Rapid and Regioselective Bromination of Anilines and Phenols

Title:o-Xylylene Bis(Triethyl Ammonium Tribromide) as a Mild and Recyclable Reagent for Rapid and Regioselective Bromination of Anilines and Phenols

Volume: 15 Issue: 8

Author(s): Roya Hemati, Ashraf S. Shahvelayati*Khadijeh Yadollahzadeh

Affiliation:

• Department of Chemistry, Yadegar-e-Imam Khomeini (RAH) Shahre-rey Branch, Islamic Azad University, Tehran,Iran

Keywords: o-Xylylene bis(triethyl ammonium tribromide), phenol, aniline, β-naphthol, bromination, recyclable regent.

Abstract: Background: o-Xylylene bis(triethyl ammonium tribromide) (OXBTEATB) as a recyclable and high bromine containing di-(tribromide) reagent has been employed for the bromination of various organic substrates such as phenol and aniline or its derivatives. This catalyst can be recovered and reused several times.

Methods: Aryl bromides shown in Table 1, were easily produced from bromination of aromatic compounds by OXBTEATB. This high-yield process lets the reagents to be recycled and reused.

Results: As shown in Table 1, substituted anilines, phenols and β-naphthol were found to be the most reactive and immediately converted to the corresponding mono-brominated products by OXBTEATB.

Conclusion: OXBTEATB can be considered a solidified bromine. This novel reagent has variable solubility in different polar protic and aprotic solvents but insoluble in non-polar aprotic solvent. Subsequently, OXBTEATB can be recognized as a more useful brominating and regioselective catalyst than the liquid bromine.

Cite this article as:

Hemati Roya , Shahvelayati S. Ashraf *, Yadollahzadeh Khadijeh , o-Xylylene Bis(Triethyl Ammonium Tribromide) as a Mild and Recyclable Reagent for Rapid and Regioselective Bromination of Anilines and Phenols, Letters in Organic Chemistry 2018; 15 (8) . https://dx.doi.org/10.2174/1570178615666180126153243