4.1 Article

The use of polymeric sulfides as catalysts for the para-regioselective chlorination of phenol and 2-chlorophenol

Journal

JOURNAL OF SULFUR CHEMISTRY
Volume 41, Issue 1, Pages 1-12

Publisher

TAYLOR & FRANCIS LTD
DOI: 10.1080/17415993.2019.1688815

Keywords

Para-regioselective chlorination; catalysts; aluminum chloride; 2; 4-dichlorophenol; phenol; poly(alkylene sulfide)s

Funding

  1. Cardiff University
  2. King Saud University
  3. Swansea University

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Various poly(alkylene sulfide)s have been synthesized and used as catalysts to enhance the para-regioselectivity in chlorination of phenol and 2-chlorophenol using freshly distilled sulfuryl chloride in the presence of AlCl3 as an activator. Poly(alkylene sulfide)s having alternating spacers, one having three methylene groups and the second having three, six or nine methylene groups were the most para-regioselective catalysts in chlorination of both phenol and 2-chlorophenol. For example, chlorination of phenol and 2-chlorophenol in the presence of optimal examples of such poly(alkylene sulfide)s gave 4-chlorophenol and 2,4-dichlorophenol as the major products in 94.8 and 95.4% yields, respectively, compared with 75.4 and 55.0% yields in the absence of catalysts. In addition, double chlorination of phenol in the presence of poly(alkylene sulfide)s gave 2,4-dichlrophenol in up to 97.1% yield compared with only 58.6% in the absence of catalysts.

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