Water → 4-(Chloromethyl)-1-fluoro-2-phenoxybenzene

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Reaction Steps

In a dry flask were placed in succession 5 ml of diethyl ether, 1.21 g (0.0102 mole) of thionyl chloride, and one drop of pyridine. A solution of 1.85 g (0.0085 mole) of (4-fluoro-3-phenoxyphenyl)methyl alcohol in 5 ml of diethyl ether was added dropwise to the reaction mixture. Upon completion of addition, the reaction mixture was heated at reflux for one hour. After being cooled to room temperature, 10 ml of water was added slowly to the reaction mixture. The phases were separated. Twice the aqueous phase was extracted with 15 ml of diethyl ether, and these extracts were combined with the organic phase. The latter was washed successively twice with 10 ml of a saturated aqueous solution of sodium chloride, once with 10 ml of an aqueous solution of sodium bicarbonate, and twice with the saturated aqueous solution of sodium chloride. After being dried over anhydrous sodium sulfate and being filtered, the solvent was evaporated under reduced pressure, leaving 1.85 g of (4-fluoro-3-phenoxyphenyl)methyl chloride as a light yellow liquid. The nmr and ir spectra were consistent with the proposed structure.

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