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

Masayuki Kirihara; Sho Yamahara; Tomohide Okada; Hiroaki Matsumuro; Yukari Kinoshita; Atsuhito Kitajima; Yuya Takamura; Tatsuya Odagiri; Tomotake Asawa; Yukihiro Sugiyama; Yoshikazu Kimura

doi:10.1055/a-1823-3604

Synthesis, Table of Contents

Synthesis 2022; 54(18): 4120-4128
DOI: 10.1055/a-1823-3604

paper

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

Masayuki Kirihara ∗

^aDepartment of Materials and Life Science, Shizuoka Institute of Science and Technology, 2200–2 Toyosawa, Fukuroi, Shizuoka 437–8555, Japan

,

Sho Yamahara

^aDepartment of Materials and Life Science, Shizuoka Institute of Science and Technology, 2200–2 Toyosawa, Fukuroi, Shizuoka 437–8555, Japan

,

Tomohide Okada

^bMarket Development Department, Nippon Light Metal Company, Ltd., 1–1–13 Shimbashi, Minato–ku, Tokyo 105–8681, Japan

,

Hiroaki Matsumuro

^aDepartment of Materials and Life Science, Shizuoka Institute of Science and Technology, 2200–2 Toyosawa, Fukuroi, Shizuoka 437–8555, Japan

,

Yukari Kinoshita

^aDepartment of Materials and Life Science, Shizuoka Institute of Science and Technology, 2200–2 Toyosawa, Fukuroi, Shizuoka 437–8555, Japan

,

Atsuhito Kitajima

^aDepartment of Materials and Life Science, Shizuoka Institute of Science and Technology, 2200–2 Toyosawa, Fukuroi, Shizuoka 437–8555, Japan

,

Yuya Takamura

^aDepartment of Materials and Life Science, Shizuoka Institute of Science and Technology, 2200–2 Toyosawa, Fukuroi, Shizuoka 437–8555, Japan

,

Tatsuya Odagiri

^cR & D Department of Chemicals, Nippon Light Metal Company, Ltd., 161 Kambara, Shimizu–ku, Shizuoka 421–3203, Japan

,

Tomotake Asawa

^dQuality Assurance Section, Nippon Light Metal Company, Ltd., 161 Kambara, Shimizu–ku, Shizuoka 421–3203, Japan

,

Yukihiro Sugiyama

^eNippon Electrode Co. Ltd., 5600 Kambara, Shimizu–ku, Shizuoka 421–3203, Japan

,

Yoshikazu Kimura ∗

^fResearch and Development Department, Iharanikkei Chemical Industry Co. Ltd., 5700–1 Kambara, Shimizu–ku, Shizuoka 421–3203, Japan

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Abstract

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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

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References

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