[Li]CCCC.[Br:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1I.[F:15][CH:16]([F:22])[C:17](OCC)=[O:18].Cl>C1COCC1>[Br:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[C:17](=[O:18])[CH:16]([F:22])[F:15]
Add n-BuLi (8.86 mL, 14.18 mmol) slowly to a solution of 2-bromo-4-fluoro-1-iodobenzene (4.27 g, 14.2 mmol) in THF (50 mL) at −100° C. over 15 min under N2. Stir the solution for 30 min. Add ethyl difluoroacetate (2.81 mL, 26.9 mmol) and stir for 3 h. Add an HCl (50 mL, 2 N) solution and warm the solution up to RT. Separate the organic layer, dry the organic layer over magnesium sulfate, and remove the solvent. Purify the residue by column chromatography (hexane:ethyl acetate/10:1) to give the title compound (2.3 g, 64%). MS (GC) m/z 252 [M]+.
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