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

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%).

1. temperatureAfter the reaction mixture was cooled to 0° C.
2. stirringthe mixture was further stirred at room temperature for 15 hours
3. extractionthe mixture was extracted with ethyl acetate
4. washthe organic layer was successively washed with water (twice) and a saturated aqueous NaCl solution
5. dry with materialdried with anhydrous sodium sulfate
6. customThe residue obtained
7. customby removing the solvent under reduced pressure
8. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=9/1)

ORD record

ord-ee1fdf0ab61d44abb9db9b7c7a3c4838

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07923573B2