Bromination of Aromatics With Pyridinium Hydrobromide Perbromide: An Organic Laboratory Experiment

TCE

The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 3 Issue 2 (1998), S1430-4171(98)02191-5

Bromination of Aromatics With Pyridinium Hydrobromide Perbromide: An Organic Laboratory Experiment

W. Preston Reeves,* Rufus M. King, II, Lynette L. Jonas, Oyvind Hatlevik, Cuong V. Lu, and Brian Schulmeier

Department of Chemistry, Texas Lutheran University, Seguin, Texas 78155

Published online: 2 April 1998

Abstract. Bromination of aniline and anisole derivatives with pyridinium hydrobromide perbromide (PHP) has been selectively achieved. By selecting appropriate reaction conditions, monobrominated, dibrominated, and, in some instances, tribrominated products may be obtained. PHP provides a safe and environmentally friendly way to conduct aromatic brominations. Pedagogic opportunities for this experiment are wide-ranging. GC-MS may be used for the separation of product mixtures. Steric and solvent effects may also be discussed as the scope and limitations of this technique are investigated in the organic laboratory.

Key Words: Laboratories and Demonstrations; organic laboratory experiment; bromination; aromatics; pyridinium hydrobromide

(*) Corresponding author. (E-mail: reeves_p@txlutheran.edu)

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