B([C:4]1[CH:5]=[CH:6][C:7]([Cl:13])=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10])(O)O.I[C:15]1[CH:16]=[C:17]([B:21]([OH:23])[OH:22])[CH:18]=[CH:19][CH:20]=1.C([O-])([O-])=O.[K+].[K+].Cl>C1(C)C=CC=CC=1.CO.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[B:21]([C:17]1[CH:16]=[C:15]([C:4]2[CH:5]=[CH:6][C:7]([Cl:13])=[C:8]([C:9]([OH:11])=[O:10])[CH:12]=2)[CH:20]=[CH:19][CH:18]=1)([OH:23])[OH:22]5-Borono-2-chlorobenzoic acid (200 mg, 1 mmol), 3-iodophenylboronic acid (125 mg, 0.5 mmol), K2CO3 (207 mg, 1.5 mmol) and PdCl2(PPh3)2 (37 mg, 0.05 mmol) were dissolved in a mixture of toluene-MeOH (17 mL:1.7 mL) and heated at 75° C. for 3 hours. The mixture was filtered through celite washed with water and the solvent was evaporated in vacuo. The formed crude residue was acidified with 2 M HCl and extracted into EtOAc and dried over anhyd. Na2SO4, evaporated solvent in vacuo to obtain crude 3′-borono-4-chlorobiphenyl-3-carboxylic acid as a reddish brown solid. The crude product was used for the next step without further purification.
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