Ammonium Chloride → 4-((5-Chloro-furan-2-yl)-hydroxy-methyl)-benzonitrile

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Reaction Conditions

Reaction Steps

To a solution of THF (40 mL) and 4-iodobenzonitrile (2.0 g) was added isopropylmagnesium chloride (2M, 6.1 mL) dropwise at −78° C. under a nitrogen atmosphere, which was stirred for 1 hour and 10 minutes at 0° C. After cooling to 78° C., 5-chloro-2-furaldehyde (1.4 g) was added dropwise thereto, which was stirred for 15 minutes at room temperature. A saturated aqueous ammonium chloride solution was added at room temperature, and then extraction was performed with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered, after which the filtrate was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1) to obtain the titled compound (2.4 g).

Provenance & Evidence