1: H2 / Pd-C 2: (i) aq. NaNO2, aq. HBr, (ii) CuBr, aq. HBr View Scheme

1: NaOMe 2: H2 / Pd-C 3: (i) aq. NaNO2, aq. HBr, (ii) CuBr, aq. HBr View Scheme

1: HNO3, H2SO4 2: NaOMe 3: H2 / Pd-C 4: (i) aq. NaNO2, aq. HBr, (ii) CuBr, aq. HBr View Scheme

(i) aq. NaNO2, aq. HBr, (ii) CuBr, aq. HBr; Multistep reaction;

(i) BuLi, hexane, (ii) /BRN= 605365/; Multistep reaction;

sodium hydrogencarbonate in hydrogen bromide; acetic acid

dicyclohexyl(2',4',6'-triisopropyl-5-methoxy-3,4,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; C50H70NO4PPdS; C50H70NO4PPdS; dicyclohexyl(2',4',6'-triisopropyl-4-methoxy-3,5,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; ammonia; sodium t-butanolate in 1,4-dioxane T=80°C; 24 h; Inert atmosphere; Overall yield = 95 percent;

1: With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.333333 h; 2: With tri-isopropoxy-borane in tetrahydrofuran; hexane T=-78 - 20°C; 3: With water; acetic acid in tetrahydrofuran; hexane T=20°C;

1: 4-bromo-1-methoxy-2-(trifluoromethyl)benzene With n-butyllithium in tetrahydrofuran; hexanes T=-78°C; 0.333333 h; 2: tri-isopropoxy-borane in tetrahydrofuran; hexanes T=-78°C; 0.5 h; 3: With acetic acid in tetrahydrofuran; hexanes; water T=20°C;