A useful magnesium reagent for the preparation of 1,1-difluoro-2-hydroxyphosphonates from diethyl bromodifluoromethylphosphonate via a metal—halogen exchange reaction - Laboratoire Hétéroéléments et Coordination (DCPH) Access content directly
Journal Articles Journal of Organometallic Chemistry Year : 1997

A useful magnesium reagent for the preparation of 1,1-difluoro-2-hydroxyphosphonates from diethyl bromodifluoromethylphosphonate via a metal—halogen exchange reaction

Abstract

When (EtO) 2 P(O)CF 2 Br (1) is treated with isopropylmagnesium chloride in THF at low temperature it gives a magnesium species (2) which undergoes reactions with strong electrophiles (HCl, TMSCl, halogens, aldehydes and ketones). The formation of products strongly depends on the reaction conditions. With 1.5 equivalents of (2) between-78°C and 0°C, a conversion of more than 90% of aldehydes and ketones into 2-hydroxyphosphonates (7) and (8) can be achieved. These compounds (7) and (8) in the presence of base (NaH, LDA) are rearranged into 2,2-difluoroethylphosphates without concomitant formation of 1,1-difluoroolefines.
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Dates and versions

hal-03166507 , version 1 (11-03-2021)

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Rachel Waschbüsch, Mohammad Samadi, Philippe Savignac. A useful magnesium reagent for the preparation of 1,1-difluoro-2-hydroxyphosphonates from diethyl bromodifluoromethylphosphonate via a metal—halogen exchange reaction. Journal of Organometallic Chemistry, 1997, 529 (1-2), pp.267-278. ⟨10.1016/S0022-328X(96)06541-2⟩. ⟨hal-03166507⟩
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