Process to bromomethylate aromatic compounds

Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Mixing of two or more solid polymers; mixing of solid...

Reexamination Certificate

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C549S029000, C570S199000

Reexamination Certificate

active

07078465

ABSTRACT:
The present invention provides a process for bromomethylation of organic compounds, wherein said process is a two stage process comprising of the following stages: a) reacting paraformaldehyde with hydrogen bromide and separating bis-bromomethyl ether (BBME) from the reaction mixture, and, b) reacting BBME obtained in stage (a) with an organic compound in the presence of a Lewis acid, to obtain the bromomethylated organic compound. Further provided by the present invention is a process for the preparation of 4,4′-bis-(diethylphosphonomethyl)-biphenyl (BPMB).

REFERENCES:
patent: 560736 (1975-04-01), None
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A. Roedig “Reaction of bis(bromomethyl)ether with aromatic compounds” Houben-Weyl (1995) V. 4, pp. 484-487.
George A Olah “Synthetic Methods and Reactions” Communications (Aug. 1974) pp. 560-561.
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Mikael Begtrup et al Equilibrium Control Bromomethylation: An Expedient Route to 2-Amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic Acid (AMPA) Synthesis (Sep. 1993) pp. 861-863.
Nupur Garg et al “Redioselective Bromomethylation of 1,2-Dialkylbenzenes” Synlett pp. 310-312.
Ried, Grabosch “Kondensation cyclischer Bis-halogenmethyl-Verbindungen mit nichtaromatischen Amines” Chemische Berichte, (1958) pp. 2485-2495.
Stephen H et al “The Introduction of the Chloromethyl Group into the Aromatic Nucleus” Journal of the Chemcial Society, Chemical Society, London, GB (1920) vol. 117, pp. 510-527.
Szendey, Munnes “Konstitution und Eigenschaften des Biphenylen-(4,4′)-bis-′methyl-atropiniumbromids!, einer biquartaren Atropinverbindung” Chemische Berichte (1961) pp. 38-42.
V. Braun “Die Einwirkung flussigen Ammoniaks auf organische Halogenverbindungen” Chemische Berichte (1937) pp. 979-993.
Jin Zavada et al “A Facile Synthesis of Hexadis(bromomethyl)benzene from Mesitylene” Synthesis p. 1132.

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