1: With n-butyllithium in tetrahydrofuran 1 h; cooling; 2: With boric acid trimethyl ester in tetrahydrofuran 2 h; cooling; 3: With hydrogenchloride in tetrahydrofuran; water

1.1: 60 percent / sodium tert-butoxide; palladium(II) acetate; tri-o-tolylphosphine / toluene / 24 h / 110 °C 2.1: n-BuLi / tetrahydrofuran / 1 h / cooling 2.2: trimethyl borate / tetrahydrofuran / 2 h / cooling 2.3: 77 percent / HCl / tetrahydrofuran; H2O View Scheme

1.1: 60 percent / sodium tert-butoxide; palladium(II) acetate; tri-o-tolylphosphine / toluene / 24 h / 110 °C 2.1: n-BuLi / tetrahydrofuran / 1 h / cooling 2.2: trimethyl borate / tetrahydrofuran / 2 h / cooling 2.3: 77 percent / HCl / tetrahydrofuran; H2O View Scheme

tetrakis(triphenylphosphine) palladium(0); potassium carbonate in tetrahydrofuran T=50°C; Suzuki cross-coupling;