[F:1][C:2]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[C:9](F)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:26][OH:27]>C1COCC1>[F:1][C:2]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[C:9]([O:27][CH3:26])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]Methyl 2,5-difluoro-4-nitrobenzoate (Apollo, 500 mg; 2.30 mmol; 1 eq.) was dissolved in MeOH (10 mL). The solution was cooled down to 0° C. Lithium bis(trimethylsilyl)amide (2.30 mL; 1 M; 2.30 mmol; 1 eq.) was added as solution in THF. After addition, the reaction mixture was stirred at RT overnight. Solvents were evaporated and the crude mixture was dissolved in EtOAc, washed with water, brine and dried over MgSO4. The resulting crude product was purified by flash chromatography (c-hex/EtOAc 90:10), affording the title product as a yellow solid. 1H NMR (CDCl3, 300 MHz) δ 7.60-7.52 (m, 2H), 3.93 (s, 3H), 3.91 (s, 3H). HPLC (Method A) Rt 3.88 min (Purity: 88.6%).
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