[F:1][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([OH:11])[C:3]=1[CH:4]=[O:5].[CH3:12][O:13][CH2:14][O:15][CH2:16][CH2:17]Br.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O.O>[F:1][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([O:11][CH2:17][CH2:16][O:15][CH2:14][O:13][CH3:12])[C:3]=1[CH:4]=[O:5]
A mixture of 2,3-difluoro-6-hydroxybenzaldehyde (2.17 g), 2-(methoxymethyloxy)-ethyl bromide (1.92 mL), potassium carbonate (2.85 g) and sodium iodide (0.41 g) in N,N-dimethylformamide (20 mL) was stirred at room temperature overnight. The reaction mixture was poured into water, and the resulting mixture was extracted with diethyl ether. The extract was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=4/1-1/1) to give 2,3-difluoro-6-[2-(methoxymethyloxy)ethoxy]benzaldehyde (1.02 g). This material was dissolved in tetrahydrofuran (15 mL). To the solution were added water (1.5 mL) and sodium borohydride (92 mg), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into 10% aqueous sodium chloride solution, and the resulting mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give the title compound (1.0 g).
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