[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:11])[CH:3]=1.C(O)(=O)C.C(O)(=O)C.[I:20]C1C=CC=CC=1.II.CN(C=O)C>CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:1][C:2]1[CH:10]=[C:9]([I:20])[C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:11])[CH:3]=1To a 250 mL flask were added 4-chloro-2-fluorobenzoic acid (4 g, 22.92 mmol), Pd(OAc)2 (0.257 g, 1.146 mmol), iodobenzene diacetate (8.12 g, 25.2 mmol), iodine (6.40 g, 25.2 mmol) and DMF (60 mL). The solution was heated under a nitrogen atmosphere at 100° C. for 20 h. LCMS showed about half of 4-chloro-2-fluorobenzoic acid was converted to the product (LCMS retention time 0.98 min, no MH+ peak). After cooling to room temperature, the solution was diluted with EtOAc and washed three times with 1 N HCl. The aqueous layers were combined and extracted once with EtOAc. The organic layers were combined, dried over Na2SO4 and concentrated to give a dark brown oil (16.4 g, 42% pure), which was taken to the next step without purification.
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