Modified and Scalable Synthesis of N‑Tosyl-4-Chlorobenzenesulfonimidoyl
Fluoride (SulfoxFluor):
Direct Imidation of Sulfinyl Chlorides with Chloramine‑T Trihydrate
Posted on 2022-02-09 - 21:30
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.
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Liu, Renxiang; Zhou, Xiao-Cong; He, Xin-Yi; Li, Yuan-Qiang; Zheng, Weiqin; Wang, Xiu; et al. (2022). Modified and Scalable Synthesis of N‑Tosyl-4-Chlorobenzenesulfonimidoyl
Fluoride (SulfoxFluor):
Direct Imidation of Sulfinyl Chlorides with Chloramine‑T Trihydrate. ACS Publications. Collection. https://doi.org/10.1021/acs.oprd.1c00431