Heterocycles p. 2739 - 2744 (2014)
Update date:2022-08-23
Topics:
Xue, Feng
Li, Chang-Gong
Zhu, Yong
Lou, Tian-Jun
He, Guang-Jie
A practical process has been developed for scalable preparation of 4-aminophenylboronic acid pinacol ester through facile two-step procedure. After boron trifluoride etherate efficiently activated the reaction of 4-bromoaniline with diphenyl ketone, metalation reaction of protected 4-bromoaniline with lithium trialkylmagnesiate readily proceeded under mild conditions (-20 °C), which was subsequently subjected to esterification and deprotection reaction to give the 4-aminophenylboronic acid pinacol ester. The improved synthetic route has been successfully scaled up to kilogram quantities in good yield and high quality.
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(2014)