C[Si]([N-][Si](C)(C)C)(C)C.[K+].[NH2:11][C:12]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:14](F)[CH:13]=1.[CH2:27]([OH:29])[CH3:28].ClCCl>C1COCC1>[NH2:11][C:12]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:14]([O:29][CH2:27][CH3:28])[CH:13]=1KHMDS (1.92 g, 9.64 mmol) was added to a mixture of ethyl 4-amino-2-fluoro-5-nitro-benzoate (2.00 g, 8.77 mmol) and ethanol (0.56 mL, 9.64 mmol) in 70 mL THF at 0° C. The mixture was stirred at 60° C. for 16 h. Then KHMDS (1.92 g, 9.64 mmol) and ethanol (1.2 mL, 20.7 mmol) were added at ambient temperature and the mixture was stirred at 60° C. for 2 h. 100 mL dichloromethane were added and the mixture extracted with sat. NH4Cl (aq). The organic layer was evaporated, the residue mixed with ethyl acetate, washed with sat. NaCl (aq), dried over Na2SO4, filtered and evaporated. The residue was purified twice by chromatography (silica gel; eluens: petrol ether/ethyl acetate=1:1 and 2:1).
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