O[CH:2]([P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])[C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.C(Cl)(Cl)Cl.C(N(S(F)(F)[F:30])CC)C>[Cl-].[Na+].O>[CH2:14]([O:13][P:12]([CH:2]([F:30])[C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1)([O:16][CH2:17][CH3:18])=[O:19])[CH3:15]To a mixture of diethyl α-hydroxy-4-nitrobenzylphosphonate (1.0 g) and chloroform (10 mL) was added diethylaminosulfur trifluoride (1.4 mL) at −78° C. and the reaction mixture was warmed to room temperature. Saturated brine was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was concentrated and the residue was purified by preparative HPLC to give 4-[(diethylphosphono)(fluoro)methyl]nitrobenzene (0.1 g, yield 10%) as yellow oil.
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