Br[C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[Cl:9].[CH3:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.CC1C(P(C2C(C)=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC1C(P(C2C(C)=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.Cl[Pd]Cl>[CH3:10][O:11][C:12]1[C:13]([C:2]2[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=2[Cl:9])=[CH:14][CH:15]=[CH:16][CH:17]=1A mixture of 1-bromo-2,6-dichlorobenzene (5.0 g, 0.022 mol), 2-methoxyphenylboronic acid (5.045 g, 0.033 mol) and potassium carbonate (7.65 g, 0.055 mol) in dioxane (130 mL) and water (13 mL) was purged with nitrogen for 20 minutes. Trans-dichlorobis(tri-o-tolylphosphine)palladium (II) (0.87 g, 0.0011 mol) was added and the reaction mixture heated to 100° C. for 36 hours. The cooled reaction mixture was then filtered through celite washing the filter cake with ethyl acetate. The combined organic filtrates were diluted to 500 mL by the addition of ethyl acetate, then washed with 2.0 M aqueous sodium hydroxide (2×350 mL), water (350 mL) and saturated brine (350 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford a yellow oil. Purification by flash chromatography using a solvent gradient of 0.5 to 2% ethyl acetate in hexane gave 2.74 g (49%) of 2′,6′-dichloro-1,1′-biphenyl-2-yl methyl ether as a white solid. MS (EI) m/z 252 (M+).
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