Microscale Synthesis of 1-Bromo-3-chloro-5-iodobenzene: An Improved Deamination of 4-Bromo-2-chloro-6-iodoaniline

Michael W. Pelter , Libbie S.W. Pelter , Dusanka Colovic and Regina Strug
Department of Chemistry and Physics, Purdue University–Calumet, Hammond, IN 46323-2094
J. Chem. Educ., 2004, 81 (1), p 111
DOI: 10.1021/ed081p111
Publication Date (Web): January 1, 2004
Benzene, Its Derivatives, and Condensed Benzenoid Compounds

Abstract

In this paper, we report the reductive deamination of 4-bromo-2-chloro-6-iodoaniline with isoamyl nitrite in N,N-dimethylformamide. This reaction can be performed successfully in an undergraduate laboratory using microscale techniques. In general, product yields averaged greater than 75%. Overall, we find this procedure to be advantageous to the published methods owing to its requirement of less starting material, higher product yields, and a greatly simplified procedure.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Feature):

The Microscale Laboratory

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Microscale Lab
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  • Received: August 03, 2009

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