[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.C(N(C(C)C)C(C)C)C.[CH2:18]([Si:20]([CH2:28][CH3:29])([CH2:26][CH3:27])[CH2:21][CH2:22][O:23][CH2:24]Cl)[CH3:19].O>C(Cl)(Cl)Cl>[Br:1][C:2]1[C:7]([O:8][CH2:24][O:23][CH2:22][CH2:21][Si:20]([CH2:26][CH3:27])([CH2:18][CH3:19])[CH2:28][CH3:29])=[CH:6][CH:5]=[CH:4][N:3]=1To a solution of 2-bromo-3-hydroxypyridine (15 g, 0.0862 mol) in chloroform (260 mL), ethyldiisopropylamine (18 mL, 0.103 mol) and 2-(triethylsilyl)ethoxymethyl chloride (16.7 mL, 0.0948 mol) were added at 0° C. After the mixture was stirred at room temperature for 2 hours, water (50 mL) was added thereto and the precipitated insoluble materials were filtered off. The organic layer of the filtrate was separated, washed with water, and then dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give 2-bromo-3-[2-(triethylsilyl)ethoxymethoxy]pyridine (20.3 g, 77%) as a light-yellow oil.
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