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

[ Vol. 15 , Issue. 8 ]

Author(s):

Roya Hemati, Ashraf S. Shahvelayati* and Khadijeh Yadollahzadeh   Pages 682 - 687 ( 6 )

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.

Keywords:

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

Affiliation:

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

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