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Synthesis 1995; 1995(9): 1102-1106
DOI: 10.1055/s-1995-4065
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3,4-Dihydroisocoumarins from α-Bromo-o-tolunitrile and Ketones or Aldehydes

Takahiro Kanda, Shinzi Kato, Takushi Sugino, Nobuaki Kambe* , Akiya Ogawa, Noboru Sonoda1
  • *Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565, Japan
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Publication Date:
31 December 2000 (online)

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o-Cyanobenzyllithium (3) was efficiently generated by lithium-tellurium exchange of the corresponding benzylic telluride 2 prepared in situ from lithium butanetellurolate and α-bromo-o-tolunitrile (1). Reaction of ketones or aldehydes with 3 afford substituted 2-hydroxyethylbenzonitriles 4 in high yields. The subsequent acid-catalyzed lactonization gave 3-substituted 3,4-dihydroisocoumarins 5 in good yields. All these successive reactions could be performed in the same reaction flask without isolation of intermediates.

butyllithium - tellurium - Li-Te exchange - benzyllithium - 3,4-dihydroisocoumarins