[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][N:14]=2)=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[Na+].Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][N:14]=2)=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]To a solution of methyl 5-chloro-2-[(5-fluoropyridin-2-yl)oxy]benzoate (204 mg, 0.72 mmol) in tetrahydrofuran (3 mL) was added 2 M sodium hydroxide aqueous solution (1.5 mL) and the reaction mixture was stirred at room temperature for 24 h. Then the reaction mixture was acidified with 2 M hydrochloric acid (2 mL). The precipitates were collected by filtration and dried under reduced pressure to afford 184 mg (95%) of the title compound: 1H-NMR (DMSO-d6) δ 8.02 (1H, d, J=3.1 Hz), 7.85–7.66 (2H, m), 7.66 (1H, dd, J=8.8, 2.8 Hz), 7.26 (1H, d, J=8.8 Hz), 7.11 (1H, dd, J=9.0, 3.5 Hz).
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