1,2-Dibromoethane → Methyl 1-(4-bromophenyl)cyclopropane-1-carboxylate

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Reaction Steps

After sodium hydride (55% oily) (2.40 g, 55.0 mmol) was added to a solution of methyl (4-bromophenyl)acetate (5.73 g, 25.0 mmol) obtained in Example (3-1) in N,N-dimethylformamide (50 ml) at 0° C., the mixture was stirred at room temperature for 10 minutes. After the reaction mixture was cooled to 0° C. and 1,2-dibromoethane (2.37 ml, 27.5 mmol) was added thereto, the mixture was further stirred at room temperature for 15 hours. After a saturated aqueous ammonium chloride solution was poured into the reaction mixture and the mixture was extracted with ethyl acetate, the organic layer was successively washed with water (twice) and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=9/1) to give methyl 1-(4-bromophenyl)cyclopropanecarboxylate as an oil (2.97 g, yield: 47%).

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