Facile synthesis of 2-bromo-3-fluorobenzonitrile: An application and study of the halodeboronation of aryl boronic acids

被引:58
作者
Szumigala, RH [1 ]
Devine, PN [1 ]
Gauthier, DR [1 ]
Volante, RP [1 ]
机构
[1] Merck & Co Inc, Dept Proc Res, Rahway, NJ 07065 USA
关键词
D O I
10.1021/jo035184p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A scaleable synthesis of 2-bromo-3-fluorobenzonitrile via the NaOMe-catalyzed bromodeboronation of 2-cyano-6-fluorophenylboronic acid was developed. The generality of this transformation was demonstrated through the halodeboronation of a series of aryl boronic acids. Both aryl bromides and aryl chlorides were formed in good to excellent yields when the corresponding aryl boronic acid was treated with 1,3-dihalo-5,5-dimethylhydantoin and 5 mol % NaOMe.
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页码:566 / 569
页数:4
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