[CH2:1]([C:3]1[C:8]([F:9])=[CH:7][C:6]([OH:10])=[C:5]([N+:11]([O-:13])=[O:12])[CH:4]=1)[CH3:2].[C:14]([O-])([O-])=O.[K+].[K+].CI.O>CS(C)=O.C(OCC)C>[CH2:1]([C:3]1[CH:4]=[C:5]([N+:11]([O-:13])=[O:12])[C:6]([O:10][CH3:14])=[CH:7][C:8]=1[F:9])[CH3:2]
4-Ethyl-5-fluoro-2-nitrophenol (5.72 g, 30.9 mmol) was dissolved in 60 mL of DMSO with stirring. K2CO3 (6.41 g, 46.4 mmol) was added. Methyl iodide (2.5 mL, 40 mmol) was added via syringe. The reaction was stirred overnight and poured into H2O and diethyl ether. The layers were separated, and the organic layer was washed with brine. The combined aqueous layers were extracted with EtOAc (2×). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography to afford 5.13 g (83%) of the title compound of step C. 1H NMR (400 MHz, DMSO-d6) δ 7.88 (d, J=7.9 Hz, 1H), 7.23 (d, J=12.1 Hz, 1H), 3.86 (s, 3H), 2.56 (q, J=7.6 Hz, 2H), 1.11 (t, J=7.5 Hz, 3H).
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