Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[F:13].C([Mg]Br)(C)C.[C:19](=[O:21])=[O:20]>C1COCC1>[F:13][C:3]1[CH:4]=[C:5]([O:8][C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:7][C:2]=1[C:19]([OH:21])=[O:20]A solution of 1-bromo-2-fluoro-4-(trifluoromethoxy)benzene (8 g, 30.8 mmol) in 170 mL of THF was cooled to −40° C., and then i-PrMgBr (0.4 mol/L in THF, 91 mL) was injected. After being stirred for 3 h, CO2 was injected for 2 h at 0° C. The mixture was washed with 1M HCl aqueous solution, separated. The aqueous layer was extracted with CH2Cl2. The combined organic layers were dried over Na2SO4, and concentrated under reduced pressure. The residue was washed with petroether to give the title compound (6 g, 87% yield): 1H NMR (400 MHz, CDCl3): δ ppm 7.05-7.12 (m, 2H), 8.10 (t, J=8.4 Hz, 1H).
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