- Characterization and Synthesis of a 6-Substituted Benzo[b]thiophene
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An impurity observed during the synthesis of zileuton (Zyflo) has been isolated and characterized as a benzo[o]thiophene derivative that has undergone electrophilic substitution in the 6 position (4). A nine-step synthesis confirms the structural assignment. Key steps in the synthesis include a regioselective Friedel-Crafts coupling between 2-hydroxythioanisole, 8, and 1-(benzo[6]thien-2-yl)ethanol, 1, and formation of a benzo[b]thiophene from an o-methylthiobenzaldehyde, 14, and chloroacetone. The synthesis provides a potentially general route to substituted benzo[6]thiophenes.
- Haight, Anthony R.,Wayne, Gregory S.,Lannoye, Gregory S.,Parekh, Shyamal I.,Zhang, Weijiang,Copp, Richard R.,Hollis, L. Steven
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p. 5903 - 5907
(2007/10/03)
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