potassium carbonate in N,N-dimethyl-formamide 2 h;

Amberlite 200 (H+ form) in acetic acid T=100°C; 7 h;

potassium carbonate in acetone 8 h; Reflux;

1: 86 percent / conc. H2SO4 / CH2Cl2 / 8 h / Ambient temperature 2: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, 20 deg C, 2 h View Scheme

1: 86 percent / conc. H2SO4 / CH2Cl2 / 8 h / Ambient temperature 2: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, 20 deg C, 2 h View Scheme

1: With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.0833333 h; 2: With boron triethoxide in tetrahydrofuran; hexane T=-78°C; 0.5 h; 3: With hydrogenchloride in tetrahydrofuran; hexane; water T=20°C;

1: 2-(1-adamantyl)-4-bromo-1-methoxybenzene With magnesium; ethylene dibromide in tetrahydrofuran RefluxInert atmosphere; 2: boric acid trimethyl ester in tetrahydrofuran T=-50 - -40°C; 0.5 h; Inert atmosphere; 3: With hydrogenchloride; water in tetrahydrofuran

magnesium; 1,2-dibromoethane; lithium chloride in tetrahydrofuran under Ar; Mg and LiCl in THF heated at 40°C, 1,2-Br2C2H4 added, 2-(1-adamantyl)-4-Br-anisole in THF added at slight boiling temp., boiling for 0.5 h, decantation, soln. added to soln. of B(OMe)3 in THF at 0-5°C, stored at 0°C (16 h); HCl and water added, mixt. extd. with Et2O, org. phase dried over Na2SO4, evapn. under vac., residue treated with EtOAc, soln. stored at 0°C overnight, ppt. filtered off, washed with cold EtOAc, dried at 100°C;

1: 2-(1-adamantyl)-4-bromo-1-methoxybenzene With magnesium; ethylene dibromide in tetrahydrofuran T=45 - 55°C; 1.5 h; 2: With zinc(II) chloride in tetrahydrofuran T=20 - 25°C; 1 h; 3: 6-bromo-naphthalene-2-carboxylic acid methyl ester With Cl2Ni(1,2-bis(diphenylphosphino)ethane) in tetrahydrofuran T=20°C; 2 h;

1: 2-(1-adamantyl)-4-bromo-1-methoxybenzene With magnesium; ethylene dibromide in tetrahydrofuran T=35 - 45°C; 0.75 h; Heating / reflux; 2: With zinc(II) chloride in tetrahydrofuran T=22 - 38°C; 1 h; 3: 2-(1-adamantyl)-4-bromo-1-methoxybenzene With palladium diacetate in tetrahydrofuran 24 h; Heating / reflux;