[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH2:15][CH3:16])[CH:12]=[CH:11][C:10]=1[O:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][C:19]=1[F:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Sn](Cl)Cl.Cl.[OH-].[Na+]>CCOCC>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH2:15][CH3:16])[CH:12]=[CH:11][C:10]=1[O:17][C:18]1[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][C:19]=1[F:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1To a solution of 2-(benzyloxy)-4-ethyl-1-(2-fluoro-4-nitro phenoxy)benzene (25 g; 68 mmol) in ether (86 mL), under argon cooled to 0° C., was added a suspension of tin dichloride (153 g; 801 mmol) in HCl (50 mL; 2 mol). The mixture was allowed to warm up to room temperature overnight, then a 10% NaOH solution was added dropwise. The resulting mixture was extracted with ethyl acetate (5*400 mL). Combined organic phases were washed with water (400 mL) and brine, then dried over Na2SO4 and concentrated. The residue was purified on silica gel (ethyl acetate/cyclohexane 1:9) to yield the title compound as a light brown solid (15.8 g; 68.8%)
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