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
- Authors: Gazizov M.B.1, Ivanova S.Y.1, Khairullin R.A.1, Kirillina Y.S.1, Gazizova K.S.1
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Affiliations:
- Kazan National Research Technological University
- Issue: Vol 88, No 11 (2018)
- Pages: 2243-2250
- Section: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/222520
- DOI: https://doi.org/10.1134/S1070363218110014
- ID: 222520
Cite item
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.
About the authors
M. B. Gazizov
Kazan National Research Technological University
Author for correspondence.
Email: mukattisg@mail.ru
Russian Federation, ul. K. Marksa 68, Kazan, Tatarstan, 420015
S. Yu. Ivanova
Kazan National Research Technological University
Email: mukattisg@mail.ru
Russian Federation, ul. K. Marksa 68, Kazan, Tatarstan, 420015
R. A. Khairullin
Kazan National Research Technological University
Email: mukattisg@mail.ru
Russian Federation, ul. K. Marksa 68, Kazan, Tatarstan, 420015
Yu. S. Kirillina
Kazan National Research Technological University
Email: mukattisg@mail.ru
Russian Federation, ul. K. Marksa 68, Kazan, Tatarstan, 420015
K. S. Gazizova
Kazan National Research Technological University
Email: mukattisg@mail.ru
Russian Federation, ul. K. Marksa 68, Kazan, Tatarstan, 420015