Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18](B2OC(C)(C)C(C)(C)O2)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].O>O1CCCC1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:2]2[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=2)=[CH:17][CH:16]=1To a solution of 1-bromo-4-(trifluoromethoxy)benzene (0.90 g, 3.7 mmol) in tetrahydrofuran (20 ml) was added a solution of 2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.36 g, 1.54 mmol) in tetrahydrofuran (10 ml), potassium carbonate (0.42 g, 3.0 mmol), [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (40 mg, 0.077 mmol) and water (0.20 ml) and the mixture refluxed under nitrogen for 19 h. The reaction mixture was tipped into water (150 ml) and extracted with ether (2×50 ml), the ether extract then dried (MgSO4) and evaporated to give a tan semi-solid (0.801 g). Purification by column chromatography (silica gel, 4:1 hexane/chloroform) afforded 4-methoxy-4′-(trifluoromethoxy)-1,1′-biphenyl (36) as a white solid (0.33 g, 80%). 1H nmr (CDCl3, 300 MHz) 3.86, s, 4-OMe; 6.99, d (8.7 Hz), H3,5; 7.26, d (8.1 Hz), H3′,5′; 7.49, d (8.7 Hz), H2,6 or H2′,6′; 7.55, d (8.7 Hz), H2′,6′ or H2,6. APCI (+ve) MS m/z 268 (M+, 80%).
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