C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:9]=[C:10]([OH:16])[CH:11]=[C:12]([F:15])[C:13]=1[F:14].Br[C:18]([F:25])([F:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20].O>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].CN(C=O)C>[F:7][C:8]1[CH:9]=[C:10]([CH:11]=[C:12]([F:15])[C:13]=1[F:14])[O:16][C:18]([F:25])([F:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20]Under a nitrogen atmosphere, 17 g of potassium carbonate and 4.0 g of TBAB were added to 18 g of 3,4,5-trifluorophenol (r-7) dissolved in 200 mL of DMF, 25.0 g of ethyl bromodifluoroacetate dissolved in 50 mL of DMF was added thereto, and the resultant mixture was stirred at 90° C. for 3 hours. A reaction mixture was poured into water, subjected to extraction with diethyl ether, and extracted organic layers were combined and washed with saturated brine, and then dried over anhydrous magnesium sulfate. A solvent was evaporated under reduced pressure, and thus 22.8 g of ethyl 2-(3,4,5-trifluorophenoxy)-2,2-difluoroacetate (compound (r-8)) was obtained.
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