1-Chloro-4-(chloromethyl)benzene → 2-Chloro-1-(4-chlorobenzyloxy)-4-(1-pyrazolyl)methylbenzene

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Reaction Steps

To a mixture of potassium carbonate (298 mg), 2-chloro-4-(1-pyrazolyl)methylphenol (300 mg) and anhydrous N,N-dimethylformamide (200 ml) was added dropwise an anhydrous N,N-dimethylformamide solution (2 ml) of 4-chlorobenzyl chloride (232 mg) at room temperature under stirring. This mixture was then stirred at the same temperature for 12 hours, and poured into ice-cooled saturated aqueous ammonium chloride solution, which was extracted with ethyl acetate. The organic layer was washed with water and then saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, which afforded 454 mg of 2-chloro-1-(4-chlorobenzyloxy)-4-(1-pyrazolyl)methylbenzene (compound 4). Yield, 95%.

Provenance & Evidence