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Synlett 1991; 1991(9): 642
DOI: 10.1055/s-1991-20824
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Improved Syntheses of 1H-Benz[f]indene

Calvin L. Becker* , Mark L. McLaughlin
  • *Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803-1804, USA
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Publication Date:
07 March 2002 (online)

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1,3-Cyclopentadiene, excess sodium hydride, and α, α, α′-tribromo-o-xylene react to give 1H-benz[f]indene in a 25% yield. α, α, α′, α′ -Tetrabromo-o-xylene, 2-cyclopenten-1-one, and excess sodium iodide react to from benz[f]indan-1-one. Lithium aluminum hydride reduction of benz[f] indan-1-one and dehydration of benz[f]indan-1-ol forms the title molecule in an overall yield of 40%