Water → 5-Bromo-2-[3-(3-methylphenyl)propoxy]benzonitrile

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Reaction Steps

Compound 15-1 (1.30 g) was dissolved in N,N-dimethylformamide (30 ml) and sodium hydride (60%, 1.04 g) was added at room temperature. After stirring for 30 min, 5-bromo-2-fluorobenzonitrile (1.00 g) was added, and the mixture was stirred at 50° C. for 4 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the object product (1.04 g) as a yellow oil.

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