Synlett 2014; 25(17): 2485-2487
DOI: 10.1055/s-0034-1379005
letter
© Georg Thieme Verlag Stuttgart · New York

Mild Benzylic Monobromination of Methyl Toluates in Aqueous CTAB

Kancharla Rajendar Reddy
Department of Chemistry, Osmania University (O.U), Hyderabad-500 007, A.P., India   Fax: +91(40)27090020   Email: kcrajannaou@yahoo.com
,
Kamatala C. Rajanna*
Department of Chemistry, Osmania University (O.U), Hyderabad-500 007, A.P., India   Fax: +91(40)27090020   Email: kcrajannaou@yahoo.com
,
Marri Venkateswarlu
Department of Chemistry, Osmania University (O.U), Hyderabad-500 007, A.P., India   Fax: +91(40)27090020   Email: kcrajannaou@yahoo.com
,
P. K. Saiprakash
Department of Chemistry, Osmania University (O.U), Hyderabad-500 007, A.P., India   Fax: +91(40)27090020   Email: kcrajannaou@yahoo.com
› Author Affiliations
Further Information

Publication History

Received: 26 June 2014

Accepted after revision: 26 July 2014

Publication Date:
26 August 2014 (online)


Abstract

A strategy has been developed for the regioselective monobromination of methyl toluates by using tert-butylhydrogen peroxide and potassium bromide (TBHP/KBr) in a cetyltrimethylammonium bromide (CTAB) micellar medium. Ultrasonic and microwave-assisted protocols recorded increased rates and product yields under mild reaction conditions, coupled with a straightforward isolation procedure.

Supporting Information

 
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  • 21 The reaction mixture was sonicated in an ultrasonic bath, with a frequency of 33 kHz and 100 W electric power rating. The final products were isolated by silica gel column chromatography using an EtOAc–hexane gradient.
  • 22 The reaction mixture was treated in a controlled microwave synthesizer (Biotage Initiator+SP Wave model, 0–200 W at 2.45 GHz, capped at 60 W during steady state) for several minutes (the reaction attained 120 °C at 1 bar pressure). The final products were isolated by column chromatography using an EtOAc–hexane gradient.