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
- 14 Downloads
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.
Keywords1,4-bis(dibromomethyl)benzene four-coordinate phosphorus acid methyl esters phosphorylation
Unable to display preview. Download preview PDF.
- 1.Gazizov, M.B., Kachalova, T.N., Karimova, R.F., Khairullin, R.A., and Sinyashin, O.G., Russ. J. Gen. Chem., 1997, vol. 67, no. 12, p. 1942.Google Scholar
- 2.Gazizov, M.B., Kachalova, T.N., Karimova, R.F., and Sinyashin, O.G., Dokl. Akad. Nauk, 1998, vol. 359, no. 5, p.644.Google Scholar
- 7.March, J., Advanced Organic Chemistry. Reactions, Mechanisms, and Structure, New York: Wiley, 1992, 4th ed.Google Scholar