[H-].[Na+].[C:3](=[O:10])([O:7][CH2:8][CH3:9])OCC.[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:13]=1[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].Cl>O1CCCC1>[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:13]=1[CH:19]([C:3]([O:7][CH2:8][CH3:9])=[O:10])[C:20]([O:22][CH2:23][CH3:24])=[O:21]Into a mixture of 7.2 g of sodium hydride (60% in oil), 17.0 g of diethyl carbonate and 150 ml of tetrahydrofuran, 26.0 g of ethyl 2-chloro-6-fluorophenylacetate were added dropwise under heating, and then refluxed under heating for 8 hours. The reaction mixture was cooled, poured into iced dil. hydrochloric acid and extracted with t-butyl methyl ether. The organic layer was washed with water, dried over sodium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 30.4 g of diethyl (2-chloro-6-fluorophenyl)malonate.
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