A Practical Synthesis of 2,6-Dicarboxyfluorenone

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Kirstin F. Warner, Ammiel Bachrach, Atiq-ur Rehman, Wayne F. K. Schnatter, Abhijit Mitra and Charles Shimanskas


Abstract

Herein, we report a new and efficient method for the large scale synthesis of 2,6-dicarboxyfluorenone 5 in 95% yield using 0.01mol% of bis(triphenylphosphine)palladium(II) chloride, (PPh3)2 PdCl2, as a catalyst, starting with the reaction of 2,5-dimethylbromobenzene and 4-bromotoluene to give 2,4,5-trimethylbiphenyl 3, followed by oxidation and then cyclization.


References

  1. (a) K. F. Warner, Dissertation Polytechnic University, 1996; (b) J. K. Stille, A. M. Echavarren and R. M. Williams, Org. Synth., 1991, 71, 97; (c) J. K. Stille and A. M. Echavarren, J. Am. Chem. Soc., 1987, 109, 5478 CrossRef CAS; (d) J. K. Stille and W. J. Scott, J. Am. Chem. Soc., 1986, 108, 3033 CrossRef CAS.
  2. T. N. Mitchell, J. Organomet. Chem., 1986, 304, 1 CrossRef CAS.
  3. A. Sekiya and N. Ishikawa, J. Organomet. Chem., 1976, 118, 349 CrossRef CAS.
  4. G. P. Roth and C. E. Fuller, J. Org. Chem., 1991, 56, 3493 CrossRef CAS.
  5. L. Friedman, Org. Synth., 1973, Coll. Vol. V, 810 Search PubMed.
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