C[C:2]1[C:3]([O:12][C:13]2[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=2[F:20])=[C:4]([CH:8]=[C:9](N)[CH:10]=1)[C:5]([OH:7])=[O:6].N([O-])=O.[Na+].[ClH:25]>O.[Cu](Cl)Cl>[Cl:25][C:9]1[CH:10]=[CH:2][C:3]([O:12][C:13]2[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=2[F:20])=[C:4]([CH:8]=1)[C:5]([OH:7])=[O:6]To a solution of methyl 5-amino-2-(2,6-difluorophenoxy)benzoic acid (step 3, 234 mg, 0.88 mmol) in 6 N hydrochloric acid (2.6 mL) was added a solution of sodium nitrite (74 mg, 1.07 mmol) in water (0.5 mL) at 0° C. for 15 min. The mixture was added to a slurry of copper chloride (120 mg) in concentrated hydrochloric acid (1.2 mL). The mixture was stirred for 1 day at room temperature. The mixture was extracted with dichloromethane. The organic layer was purified by column chromatography on silica gel eluting with dichloromethane/methanol (10/1) to afford 210 mg (84%) of the title compound as white solids: 1H-NMR (CDCl3) δ 7.77 (1H, d, J=2.7 Hz), 7.51 (1H, dd, J=9.0, 2.7 Hz), 7.40–7.20 (3H, m), 6.80 (1H, d, J=9.0 Hz).
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