A new approach towards synthesis of benzo[b]fluorene core

Jane B. Bogdanov

Abstract


New approach towards synthesis of  benzo[b]fluorene core is described.  The model compound, 10-methoxy-11H-benzo[b]fluoren-11-one was prepared in five steps starting from dibenzylmalonic acid.  The key step was the metal catalyzed rearrangement of 3,3’-dihalo-2,2’-spirobiindan-1,1’-dione. The choice and proper activation of the metal was critical for the assembly of the benzo[b]fluorenone system. The zinc mediated rearrangement of the corresponding dibromo derivative led to the 10-hydroxy-11H-benzo[b]fluoren-11-one derivative in 52% yield.  The structure of the product was established by spectroscopic methods and was additionally confirmed by standard methylation reaction to the 10-methoxy derivative, which is known in the literature.

Keywords


Synthesis, benzo[b]fluorenone, rearrangement

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References


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DOI: http://dx.doi.org/10.20450/mjcce.2014.495

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