[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:7]=[C:8]([Cl:16])[C:9]=1[O:10][CH2:11][C:12]([F:15])([F:14])[F:13].Br[CH2:24][CH2:25][CH2:26]Br>CN(C=O)C>[Br:3][C:4]1[CH:5]=[C:6]([C:17]2([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:26][CH2:25][CH2:24]2)[CH:7]=[C:8]([Cl:16])[C:9]=1[O:10][CH2:11][C:12]([F:15])([F:13])[F:14]To a suspension of NaH (0.65 g, 60% in paraffin oil) in DMF (100 mL), slowly added a mixture of ethyl 2-(3-bromo-5-chloro-4-(2,2,2-trifluoroethoxy)phenyl)acetate (3.0 g, 6.8 mmol) and 1,3-dibromo propane (1.61 g, 8.0 mmol) dissolved in DMF (20 mL) at 0° C. for 15 min under an atmosphere of nitrogen. The reaction mixture was allowed stir at 0° C. for 15 min, upon which the reaction mixture was poured onto crushed ice and extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by Flash column chromatography to give ethyl 1-(3-bromo-5-chloro-4-(2,2,2-trifluoroethoxy)phenyl)cyclobutanecarboxylate (2.12 g) as a thick syrup.
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