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Russian Journal of General Chemistry

, Volume 88, Issue 11, pp 2243–2250 | Cite as

Synthesis of 4-(Dibromomethyl)benzaldehyde by Catalytic Debromophosphoryl- and Phosphonyloxylation of 1,4-Bis(dibromomethyl)benzene with Phosphorus(IV) Acid Methyl Esters and Its Properties

  • M. B. GazizovEmail author
  • S. Yu. Ivanova
  • R. A. Khairullin
  • Yu. S. Kirillina
  • K. S. Gazizova
Article
  • 14 Downloads

Abstract

A new procedure has been developed for the simultaneous preparation of terephthalaldehyde and 4-(dibromomethyl)benzaldehyde by catalytic debromophosphoryl- and phosphonyloxylation of 1,4-bis- (dibromomethyl)benzene with P(IV) acid methyl esters. The reaction of 4-(dibromomethyl)benzaldehyde with ortho esters in the presence of sulfuric acid gave the corresponding acetals, whereas in the presence of ZnCl2 terephthalaldehyde bis-acetals were formed. 4-(Dibromomethyl)benzaldehyde and its acetal were converted to methyl 4-(dibromomethyl)- and 4-(dimethoxymethyl)benzoates which were phosphorylated by the action of chlorophosphines, as well as by successive treatment with phosphorus(III) chloride and P(III) esters.

Keywords

1,4-bis(dibromomethyl)benzene four-coordinate phosphorus acid methyl esters phosphorylation 

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Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • M. B. Gazizov
    • 1
    Email author
  • S. Yu. Ivanova
    • 1
  • R. A. Khairullin
    • 1
  • Yu. S. Kirillina
    • 1
  • K. S. Gazizova
    • 1
  1. 1.Kazan National Research Technological UniversityKazan, TatarstanRussia

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