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Facile Synthesis of 2-Bromo-3-fluorobenzonitrile: An Application and Study of the Halodeboronation of Aryl Boronic Acids
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2003-12-23 00:00:00 , DOI: 10.1021/jo035184p Ronald H. Szumigala, 1 , Paul N. Devine 1 , Donald R. Gauthier 1 , R. P. Volante 1
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2003-12-23 00:00:00 , DOI: 10.1021/jo035184p Ronald H. Szumigala, 1 , Paul N. Devine 1 , Donald R. Gauthier 1 , R. P. Volante 1
Affiliation
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.
中文翻译:
轻松合成2-溴-3-氟苄腈:芳基硼酸卤代硼化的应用和研究
通过NaOMe催化的2-氰基-6-氟苯基硼酸的溴代硼烷的可规模合成2-溴-3-氟苄腈的方法得到了发展。通过一系列芳基硼酸的卤代硼烷化证明了这种转化的普遍性。当将相应的芳基硼酸用1,3-二卤代5,5-二甲基乙内酰脲和5mol%的NaOMe处理时,芳基溴化物和芳基氯化物均以良好至优异的产率形成。
更新日期:2003-12-23
中文翻译:
轻松合成2-溴-3-氟苄腈:芳基硼酸卤代硼化的应用和研究
通过NaOMe催化的2-氰基-6-氟苯基硼酸的溴代硼烷的可规模合成2-溴-3-氟苄腈的方法得到了发展。通过一系列芳基硼酸的卤代硼烷化证明了这种转化的普遍性。当将相应的芳基硼酸用1,3-二卤代5,5-二甲基乙内酰脲和5mol%的NaOMe处理时,芳基溴化物和芳基氯化物均以良好至优异的产率形成。