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Vol. 26 No. 21 (2014): Vol 26 Issue 21

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Synthesis and Characterization of Novel (E)-1-(Hexa-3,5-dien-1-yl)-4-methoxybenzene via Boronate Complex

https://doi.org/10.14233/ajchem.2014.17095
Habib Hussain
Department of Chemistry, University of Engineering and Technology, Lahore, Pakistan
Syeda Rubina Gilani
Department of Chemistry, University of Engineering and Technology, Lahore, Pakistan
Zulfiqar Ali
Department of Chemistry, University of Engineering and Technology, Lahore, Pakistan
Hajira Rehman
Department of Chemistry, University of Punjab, Lahore, Pakistan
Imdad Hussain
Department of Chemistry, University of Engineering and Technology, Lahore, Pakistan

Corresponding Author(s) : Habib Hussain

hbubak@gmail.com

Asian Journal of Chemistry, Vol. 26 No. 21 (2014): Vol 26 Issue 21

Abstract

Novel (E)-1-(hexa-3,5-dien-1-yl)-4-methoxybenzene was synthesized through boronate complex. 3-(4-Methoxyphenyl)propyl diisopropylcarbamate was reacted with allylboronic acid pinacol ester in the presence of N,N,N,N-tetramethylethyllenediamine to give secondary boronic ester which was further reacted with (vinylsulfonyl)benzene by using Grubbs Hoveyda II. Resulting product (E)-2-(1-(4-methoxyphenyl)-6-(phenylsulfonyl)hex-5-en-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was then treated with 1-bromo-3,5-bis(trifluoromethyl)benzene in the presence of n-BuLi to get nucleophilic boronate complex. (E)-1-(hexa-3,5-dien-1-yl)-4-methoxybenzene was obtained in excellent yields by stirring boronate complex at 50 °C for 1 h and refluxing for 15 h.

Keywords

Lithiation borylation Secondary boronic ester 1-Bromo-3,5- bis(trifluoromethyl)benzene Boronate complex
Hussain, H., Rubina Gilani, S., Ali, Z., Rehman, H., & Hussain, I. (2014). Synthesis and Characterization of Novel (E)-1-(Hexa-3,5-dien-1-yl)-4-methoxybenzene via Boronate Complex. Asian Journal of Chemistry, 26(21), 7401–7403. https://doi.org/10.14233/ajchem.2014.17095
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