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One-Pot Synthesis of 1-[(Triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one (TIPS-EBX): Process Safety Assessment and Impact of Impurities on Product Stability
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2019-12-24 , DOI: 10.1021/acs.oprd.9b00498
Durga Prasad Hari 1 , Paola Caramenti 1 , Lionel Schouwey 1 , Miyeon Chang 1 , Stefano Nicolai 1 , Donald Bachert 2 , Timothy Wright 2 , Chuck Orella 2 , Jerome Waser 1
Affiliation  

The hypervalent iodine reagent 1-[(TriIsoPropylSilyl)Ethynyl]-1,2-BenziodoXol-3(1H)-one (TIPS-EBX) is among the most useful electrophilic and somophilic alkynylation reagents. Herein, we report a new synthetic protocol to access this reagent in one step from standard commercially available reagents. Thermal analysis of the synthesis procedure showed only weak exotherms. The compound could be obtained with high purity and stability using this new protocol, but care had to be taken to remove tosylate salts impurities, as they led to a lower thermal stability. TIPS-EBX synthesized using the new procedure displayed no shock sensitivity.

中文翻译:

一锅合成1-[(三异丙基甲硅烷基)乙炔基] -1,2-苯并三唑-3(1 H)-一(TIPS-EBX):工艺安全性评估和杂质对产品稳定性的影响

高价碘试剂1-[((TriIsoPropylSilyl)乙炔基] -1,2-苯并碘醇-3(1 H)-one(TIPS-EBX)是最有用的亲电子和亲嗜性烷基化试剂。在此,我们报告了一种新的合成方案,可从标准市售试剂中一步获得该试剂。合成过程的热分析仅显示出微弱的放热。使用该新方案可以以高纯度和稳定性获得该化合物,但是必须小心除去甲苯磺酸盐杂质,因为它们会导致较低的热稳定性。使用新程序合成的TIPS-EBX没有显示出震动敏感性。
更新日期:2019-12-25
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