Sodium Iodide → (2-(4-Bromophenoxy)ethyl)dimethylamine

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4-Bromophenol (10.0 g, 57.8 mmol) and 2-dimethylaminoethyl chloride hydrochloride (8.33 g, 57.8 mmol) were dissolved in DMF (200 ml), and potassium carbonate (24.0 g, 173 mmol) and sodium iodide (0.87 g, 5.78 mmol) were added under ice-cooling. The mixture was stirred for 13 hr at room temperature and at 70° C. for 3 hr. Water (400 ml) was added to the reaction mixture and the mixture was extracted with chloroform (2×200 ml). The organic layer was washed successively with water (2×200 ml) and saturated brine (200 ml), dried over anhydrous magnesium sulfate and concentrated. The obtained residue was dissolved in 1N hydrochloric acid (100 ml) and washed with ethyl acetate (2×200 ml). Sodium hydroxide (4 g) was added to the aqueous layer to make the layer alkaline, and the mixture was extracted with chloroform (2×200 ml). The organic layer was dried over anhydrous magnesium sulfate and concentrated. Hexane was added to the obtained residue and insoluble matter was filtered off. The mother liquor was concentrated to give the title compound (5.25 g, 37%) as a transparent oil.

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