Replacement of chlorinated solvents in the synthesis of pharmaceutical intermediates by Friedel-Crafts acylation and Fries rearrangement

Authors

  • Roser Pleixats Universitat Autònoma de Barcelona
  • Jordi Salabert Universitat Autònoma de Barcelona
  • Marc Planellas Universitat Autònoma de Barcelona
  • Guillem Fernández Universitat Autònoma de Barcelona
  • Francesca Pajuelo Almirall, S. A.
  • Francisco Sánchez-Izquierdo Almirall, S. A.

Keywords:

Solvent-free conditions, ethyl acetate, Friedel-Crafts acylation, class 3 solvent, pharmaceutical intermediates, replacement of 1, 2-dichloroethane, Fries rearrangement.

Abstract

1,2-dichloroethane has been replaced by ethyl acetate in a Friedel-Crafts acylation promoted by FeCl3, thus providing a greener procedure for the preparation of a useful pharmaceutical intermediate. In addition, the AlCl3-promoted Fries rearrangement of an O-acetyl quinolone derivative at 165 ºC under solvent-free conditions selectively provides the ortho regioisomer, in contrast with the reported procedure in 1,2-dichloroethane at 85 ºC which provides the para isomer.

Keywords: Solvent-free conditions, ethyl acetate, Friedel-Crafts acylation, class 3 solvent, pharmaceutical intermediates, replacement of 1,2-dichloroethane, Fries rearrangement.

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Author Biographies

Roser Pleixats, Universitat Autònoma de Barcelona

Jordi Salabert, Universitat Autònoma de Barcelona

Marc Planellas, Universitat Autònoma de Barcelona

Guillem Fernández, Universitat Autònoma de Barcelona

Francesca Pajuelo, Almirall, S. A.

Francisco Sánchez-Izquierdo, Almirall, S. A.

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Issue

No. 16 (2017)

Section

Articles

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