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Modified and Scalable Synthesis of N-Tosyl-4-Chlorobenzenesulfonimidoyl Fluoride (SulfoxFluor): Direct Imidation of Sulfinyl Chlorides with Chloramine-T Trihydrate
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2022-02-09 , DOI: 10.1021/acs.oprd.1c00431
Renxiang Liu 1 , Xiao-Cong Zhou 2, 3 , Xin-Yi He 2 , Yuan-Qiang Li 2 , Weiqin Zheng 1 , Xiu Wang 1 , Junkai Guo 1 , Chuanfa Ni 1 , Jinbo Hu 1
Affiliation  

N-Tosyl-4-chlorobenzenesulfonimidoyl fluoride (SulfoxFluor) has emerged as a new fluorination reagent that can be used in the rapid deoxyfluorination of various alcohols. We disclose in this article a general and practical method for the preparation of SulfoxFluor and its adaption to a large scale. Starting from readily available 4-chlorobenzenesulfonyl chloride, chloramine-T trihydrate, and potassium fluoride, SulfoxFluor was prepared on a hectogram scale in 63% overall yield with simple purification techniques. The use of chloramine-T trihydrate (instead of anhydrous chloramine-T) is a significant improvement over previous work, which streamlines the process and avoids the risk of explosion during drying or heating. This research not only establishes a reliable method for the scale-up synthesis of SulfoxFluor but also provides an insight into the imidation of sulfinyl chlorides with chloramine-T in the presence of water.

中文翻译:

N-Tosyl-4-Chlorobenzosulfonimidoyl Fluoride (SulfoxFluor) 的改性和可扩展合成:用 Chloramine-T Trihydrate 直接酰亚胺化亚磺酰氯

ñ-Tosyl-4-chlorobenzosulfonimidoyl fluoride (SulfoxFluor) 作为一种新型氟化试剂应运而生,可用于各种醇类的快速脱氧氟化。我们在本文中公开了一种通用且实用的方法,用于制备 SulfoxFluor 及其大规模适应。从容易获得的 4-氯苯磺酰氯、氯胺-T 三水合物和氟化钾开始,通过简单的纯化技术,以 63% 的总产率以百克规模制备了 SulfoxFluor。与之前的工作相比,使用三水合氯胺-T(而不是无水氯胺-T)是一项重大改进,它简化了工艺并避免了在干燥或加热过程中发生爆炸的风险。
更新日期:2022-02-09
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