[F:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[H-].[Na+].[C:11]([NH:14][C:15]1[C:16](N)=[C:17]([N+:22]([O-:24])=[O:23])[CH:18]=[CH:19][C:20]=1F)(=[O:13])[CH3:12].[Cl-:26].[NH4+]>C1COCC1.O>[C:11]([NH:14][C:15]1[C:16]([Cl:26])=[C:17]([N+:22]([O-:24])=[O:23])[CH:18]=[CH:19][C:20]=1[S:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)(=[O:13])[CH3:12]
4-Fluorobenzenethiol (0.128 ml) was added dropwise to a stirred suspension of sodium hydride (0.049 g of a 60% dispersion in mineral oil) in THF (3 ml). The mixture was stirred for 30 minutes then added dropwise to a stirred and cooled (−65° C.) solution of 3-acetamido-2-amino-4-fluoronitrobenzene (0.233 g) in THF (2 ml). The mixture was stirred for 3 hours at −65° C. then allowed to warm to ambient temperature. Saturated aqueous ammonium chloride solution (5 ml), then water (5 ml) were added and the mixture was extracted with ether (2×25 ml). The extracts were combined, washed with water (25 ml) and brine (25 ml), then dried. Volatile material was removed by evaporation and the residue was purified on a silica gel Mega Bond Elut column eluting with 0-40% EtOAc/isohexane to give the title compound. Chromatography on a Biotage cartridge (40 g silica), eluting with 40% EtOAc/isohexane to give the title compound (0.193 g) as a solid. NMR: 2.14 (s, 3H), 6.76 (d, 1H), 7.4 (t, 2H), 7.6 (m, 2H), 7.88 (d, 1H), 10.1 (brs, 1H); m/z: 339.
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