Water → 4-(Trifluoromethoxy)-4'-methoxy-1,1'-biphenyl

To 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%).

1. temperaturethe mixture refluxed under nitrogen for 19 h
2. extractionextracted with ether (2×50 ml)
3. extractionthe ether extract
4. dry with materialthen dried (MgSO4)
5. customevaporated

ORD record

ord-264939122f4147899685375cb376787d

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07863313B2