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A Convenient Preparation of N,N-Dibromoamines

Robert C. Zawalski, Peter Kovacic

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Abstract

The preparation of N,N-dibromo compounds by treatment of the parent amine or amide with free bromine,3 hypobromite solution,4 acetyl hypobromite5 or monobromoacetamide6 has been described. More recently, a method involving treatment of the free amide or amine with an N-bromo heterocycle, such as N-bromosuccinimide (NBS), has been developed.7 From our own experience, with the possible exception of the N-bromo amide or imide route, these methods tend to be highly specific, and cannot be reliably used as a general preparation of N,N-dibromoamines.

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What this paper is about

The preparation of N,N-dibromo compounds by treatment of the parent amine or amide with free bromine,3 hypobromite solution,4 acetyl hypobromite5 or monobromoacetamide6 has been described. More recently, a method involving treatment of the free amide or amine with an N-bromo heterocycle, such as N-bromosuccinimide (NBS), has been developed.7 From our own experience, with the possible exception of the N-bromo amide or imide route, these methods tend to be highly specific, and cannot be reliably used as a general preparation of N,N-dibromoamines.

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OpenAlex reports 3 citations for this work. Citation counts describe recorded attention and do not establish research quality.

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Available abstract

The preparation of N,N-dibromo compounds by treatment of the parent amine or amide with free bromine,3 hypobromite solution,4 acetyl hypobromite5 or monobromoacetamide6 has been described. More recently, a method involving treatment of the free amide or amine with an N-bromo heterocycle, such as N-bromosuccinimide (NBS), has been developed.7 From our own experience, with the possible exception of the N-bromo amide or imide route, these methods tend to be highly specific, and cannot be reliably used as a general preparation of N,N-dibromoamines.

Key concepts: Chemistry, Amide, Amine gas treating, Bromine, Imide, Organic chemistry, Halogenation, Combinatorial chemistry

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