Efficient electrophilic cobromination of alkenes and bromination of activated arenes with bromodichloroisocyanuric acid under mild conditions

被引：40
作者：
de Almeida, Leonardo S. [1 ]
Esteves, Pierre M. [1 ]
de Mattos, Marcio C. S. [1 ]
机构：
[1] Univ Fed Rio de Janeiro, Dept Quim Organ, Inst Quim, BR-21945970 Rio De Janeiro, Brazil
来源：
SYNLETT | 2007年 / 11期
关键词：
alkenes; arenes; electrophilic addition; electrophilic aromatic substitution; halogenation;
D O I：
10.1055/s-2007-982575
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Efficient methodologies for the preparation of bromodichloroisocyanuric acid were developed (70-75%). This new reagent is very efficient for regioselective electrophilic bromination of activated arenes (86-93%) and cobromination of alkenes with oxygenated nucleophiles (31-98%). The reaction of bromodichloroisocyanuric acid with anisole, acetanilide, AT-methylacetanilide leads to 4-substituted monobromoarene and with 2-methoxynaphthalene leads to 1-bromo-2-methoxynaphthalene. Alkenes were cobrominated in the presence of oxygenated nucleophilic solvents (water, alcohols, and acetic acid), leading to the corresponding bromohydrins, beta-bromoethers and beta-bromoacetates.
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页码：1687 / 1690
页数：4
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