1: in tetrahydrofuran; hexanes; toluene T=-70 - -55°C; 4.5 h; 2: With sulfuric acid; water in tetrahydrofuran; hexanes; toluene T=-35°C; pH=~ 2;

1: 4-isopropyl-2-bromo-5-fluoroanisole With n-butyllithium; tri-isopropoxy-borane in tetrahydrofuran; hexane; toluene T=-80 - -10°C; 1 h; Inert atmosphere; 2: (2-chloro-5-(trifluoromethyl)phenyl)methanol With 1,1'-bis(di-tert-butylphosphino)ferrocene palladium dichloride in tetrahydrofuran; hexane; water; toluene T=20°C; Suzuki Coupling; 12 h;

1: 4-isopropyl-2-bromo-5-fluoroanisole With n-butyllithium; tri-isopropoxy-borane in tetrahydrofuran; hexane; toluene T=-80 - -10°C; 1 h; Inert atmosphere; 2: (2-bromo-5-(trifluoromethyl)phenyl)methanol With 1,1'-bis(di-tert-butylphosphino)ferrocene palladium dichloride in tetrahydrofuran; hexane; water; toluene T=20°C; Suzuki Coupling; 12 h;

1.1: potassium phosphate; [Ru(II)(η6-benzene)(μ-Cl)Cl]2; potassium acetate; triphenylphosphine / 1-methyl-pyrrolidin-2-one / 9 h / 110 - 130 °C / Inert atmosphere; Large scale reaction 2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.75 h / 20 - 62 °C / Inert atmosphere; Large scale reaction 3.1: sodium tetrahydroborate / tetrahydrofuran; water / 17.92 h / 0 - 22 °C / Inert atmosphere; Large scale reaction 3.2: 0 - 20 °C / Inert atmosphere; Large scale reaction View Scheme