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Synthesis 2000; 2000(4): 576-580
DOI: 10.1055/s-2000-6375
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Controlled Monohalogenation of Phosphonates, Part II: Preparation of Pure Diethyl α-Monohalogenated Alkylphosphonates

Bogdan Iorga* , Frédéric Eymery, Philippe Savignac
  • *Laboratoire Hétéroéléments et Coordination, UMR CNRS 7653, DCPH, Ecole Polytechnique, 91128 Palaiseau Cedex, France; Fax +3 31 69 33 39 90; E-mail: dcph@poly.polytechnique.fr
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Publication Date:
31 December 2000 (online)

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The reaction of diethyl alkylphosphonates with chlorotrimethylsilane in the presence of lithium diisopropylamide leads to the corresponding diethyl 1-lithio(trimethylsilyl)alkylphosphonates which are cleanly halogenated (X = F, Cl, Br, I) with electrophilic reagents and then deprotected to give pure diethyl α-monohalogenalkylphosphonates. The reaction has been extended by the one-pot conversion of triethyl phosphate into diethyl α-monohalogenobutylphosphonates in 85-97% overall yields.

diethyl alkylphosphonates - electrophilic halogenating agents - lithium diisopropylamide - triethyl phosphate - diethyl α-monohalogenoalkylphosphonates