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Isothiazoles IX. Halogenation of 2‐substituted‐4‐isothiazolin‐3‐ones
Author(s) -
Weiler Ernest D.,
Petigara Ramesh B.,
Wolfersberger Martha H.,
Miller George A.
Publication year - 1977
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570140418
Subject(s) - halogenation , chemistry , medicinal chemistry , organic chemistry
Abstract Bromination of 4‐isothiazolin‐3‐ones, I, gave the 4‐bromo derivatives, III, in good yields, while formation of 4,5‐dibromo derivatives, IV, was much more difficult. In contrast, chlorination of I, even under mild conditions, gave primarily 4,5‐dichloro derivatives, VI, and lesser amounts of the 4‐chloro derivatives, V. Vigorous bromination of the 4‐methyl analog of I gave the 5‐bromo derivatives, VIII, whereas mild chlorination gave predominantly the 4,5,5‐trichloro derivatives, X.