[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:18]([S-:20])#[N:19].[K+].BrBr.[NH4+].[OH-]>CC(O)=O.O>[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][C:9]2[CH:15]=[CH:14][C:12]3[N:13]=[C:18]([NH2:19])[S:20][C:11]=3[CH:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]
To a solution of 4-(4-nitrophenoxy)aniline (Intermediate 10–1.15 g, 5.0 mmol) in AcOH (5 mL) was added KSCN (729 mg, 7.5 mmol). The mixture was cooled to 0° C. and added a solution of Br2 (256 μL, 5.0 mmol) in AcOH (6 mL) then stirred at room temperature overnight. The mixture was poured into H2O, basified with NH4OH (aq), then extracted with ethyl acetate. The organic layer was washed with water and brine, dried over Na2SO4 then evaporated. Sequence purification on SiO2 column chromatography gave Intermediate 10A (941.5 mg, 66%): MS m/e 288 (M+1) and Intermediate 10B (223.7 mg, 12%): MS m/e 366, 368 (M+1).
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