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Bischler-Möhlau indole synthesis
Additional recommended knowledge
In spite of its long history, this classical reaction has received relatively little attention in comparison with other methods for indole synthesis, perhaps owing to the harsh reaction conditions that it requires. Recently, milder methods have been developed, including the use of lithium bromide as a catalyst and an improved procedure involving the use of microwave irradiation.
For a reaction with such simple starting materials, the reaction mechanism is surprisingly complex. The first two step involve the reaction of the α-bromo-acetophenone with molecules of aniline to form intermediate 4. The charged aniline forms a decent enough leaving group for an electrophilic cyclization to form intermediate 5, which quickly aromatizes and tautomerizes to give the desired indole 7.
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Bischler-Möhlau_indole_synthesis". A list of authors is available in Wikipedia.|