Synthesis of Sulfonyl Halides from Disulfides or Thiols Using Sodium Hypochlorite Pentahydrate (NaOCl·5H₂O) Crystals

Abstract

Synthesis of sulfonyl halides using sodium hypochlorite pentahydrate (NaOCl·5H₂O) crystals was studied in detail, considering the reaction rate and yield of the desired product. NaOCl·5H₂O reacted with disulfides or thiols in acetic acid to produce sulfonyl chlorides. The yields of the desired sulfonyl chlorides were enhanced when the reaction was performed in (trifluoromethyl)benzene under a CO₂ atmosphere. The generation of hypochlorous acid (HOCl) was essential for both reactions. Similarly, sulfonyl bromides were prepared via the reaction of disulfides or thiols with sodium bromide and NaOCl·5H₂O crystals in acetic acid owing to the generation of hypobromous acid (HOBr). However, the reaction could not proceed in (trifluoromethyl)benzene under a CO₂ atmosphere because bromine was produced instead of HOBr.

Key words

sulfonyl chlorides - sulfonyl bromides - sodium hypochlorite pentahydrate - acetic acid - CO₂ atmosphere - disulfide - thiol

Publication History

Received: 18 March 2022

Accepted after revision: 12 April 2022

Accepted Manuscript online:
12 April 2022

Article published online:
31 May 2022

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Synthetic reactions using NaOCl·5H₂O recently developed by other groups:
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