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Polystyrene supported bromoderivative of 2-oxazolidone – an efficient reagent for microwave assisted bromination reactions

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Abstract

We present herein the synthesis and structural characterization of a novel, recyclable and microwave stable polymeric reagent prepared by anchoring bromoderivative of oxazolidone into the 3D matrix of divinylbenzene crosslinked polystyrene and its application for the bromination of alkenes, activated aromatic compounds and for the α-halogenation of ketones under microwave irradiation. The advantages of this protocol include a simple workup procedure, high product yield, shorter reaction time as well as solvent-free reaction pathway. Besides, this new resin was stable under standard laboratory conditions and can be kept for several months without any significant loss of activity.

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Acknowledgements

The financial assistance to Anjaly Mathew from University Grants Commission, Government of India under minor research project, is gratefully acknowledged. The authors would like to thank SAIF STIC, CUSAT, Kerala, India for characterization facilities.

Funding

This work was supported by the University Grants Commission Government of India, under the Minor Research Project. [No. 2265-MRP /15–16/KLCA029/UGC-SWRO dated 25th April 2016].

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Authors and Affiliations

  1. Department of Chemistry, Sreeneelakanta Govt.Sanskrit College, Pattambi, Palakkad, 679306, Kerala, India

    Anjaly Mathew

  2. School of Chemical Sciences, Mahatma Gandhi University, Priyadarshini Hills P.O., Kottayam, 685560, Kerala, India

    Beena Mathew

  3. Department of Chemistry, St. Joseph’s College Moolamattom, Arakulam, Idukki, 685591, Kerala, India

    Ebey P Koshy

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  1. Anjaly Mathew
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Correspondence to Ebey P Koshy.

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Highlights

• Divinylbenzene crosslinked polysterene supported bromoderivative of 2 –oxazolidone (DVB-PS-OX-Br) is an efficient, recyclable, microwave-safe and an environmentally stable reservoir of bromine

• DVB-PS-OX-Br is used for the bromination of alkenes, activated aromatic compounds and for the α-bromination of ketones under microwave irradiation

Electronic supplementary material

10965_2020_2251_MOESM1_ESM.docx

Figure S1 GC-MS spectra of bromostyrene Fig.S2 GC-MS spectra of α-Bromo cinnamaldehyde Fig.S3 GC-MS spectra of Styrene dibromide Fig.S4 GC-MS spectra of Dibromo cyclohexane Fig.S5 GC-MS spectra of 4-Bromo-N,N-dimethylaniline Fig.S6 GC-MS spectra of 4-Bromo-2,6-Dimethyl phenol Fig.S7 GC-MS spectra of 2,6-Dibromo-4-tert-butyl phenol Fig.S8 GC-MS spectra of α-Bromoacetanilide Fig. S9 1H NMR spectrum of β-Bromostyrene Fig. S10 1H NMR spectrum of Styrenedibromide (DOCX 733 kb)

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Mathew, A., Mathew, B. & Koshy, E.P. Polystyrene supported bromoderivative of 2-oxazolidone – an efficient reagent for microwave assisted bromination reactions. J Polym Res 27, 271 (2020). https://doi.org/10.1007/s10965-020-02251-w

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