[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:6][CH:5]=1.Br[CH2:16][CH2:17]Br.[Cl-].[NH4+]>CN(C)C=O>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2([C:11]([O:13][CH3:14])=[O:12])[CH2:17][CH2:16]2)=[CH:8][CH:9]=1
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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