1-bromo-2-(phenylmethoxy)naphthalene; C38H52Cl2N8O4Pd; potassium carbonate in tetrahydrofuran T=75°C;

1: With n-butyllithium in diethyl ether; hexane T=0°C; 1.5 h; 2: With boric acid trimethyl ester in diethyl ether; hexane T=20°C; 3: With hydrogenchloride in diethyl ether; hexane T=20°C; 1.5 h;

1: With n-butyllithium in diethyl ether; hexane T=-78 - 0°C; Metallation; lithiation; 2: With boric acid trimethyl ester in diethyl ether; hexane T=-78 - 20°C; Substitution; 3: With hydrogenchloride in diethyl ether; hexane; water T=20°C; Hydrolysis; 0.75 h; Title compound not separated from byproducts;

1.1: 93 percent / potassium carbonate / dimethylformamide / 5 h / 60 °C 2.1: n-butyllithium / diethyl ether; hexane / -78 - 0 °C 2.2: trimethyl borate / diethyl ether; hexane / -78 - 20 °C 2.3: HCl / diethyl ether; hexane; H2O / 0.75 h / 20 °C View Scheme

1.1: 93 percent / potassium carbonate / dimethylformamide / 5 h / 60 °C 2.1: n-butyllithium / diethyl ether; hexane / -78 - 0 °C 2.2: trimethyl borate / diethyl ether; hexane / -78 - 20 °C 2.3: HCl / diethyl ether; hexane; H2O / 0.75 h / 20 °C View Scheme