potassium hydrogencarbonate; bis(benzonitrile)palladium(II) dichloride in water; N,N-dimethyl-formamide T=100°C; 24 h;

1: With boron tribromide in dichloromethane T=0 - 20°C; Inert atmosphere; 2: With water in dichloromethane T=20°C; 1 h; Inert atmosphere;

sodium hydroxide T=100°C; 3.5 h;

pyridine; titanium tetrachloride; zinc in tetrahydrofuran Cross McMurry reaction; 32 h; Heating;

pyridine; titanium tetrachloride; zinc in tetrahydrofuran McMurry cross coupling reaction; Heating;

titanium tetrachloride; zinc in tetrahydrofuran T=0°C; Inert atmosphereReflux;

hydrogen bromide; acetic acid 1) 6 h, 2) overnight, 30 deg C;

1: 88 percent / pyridine / 1) 1 h, 2) overnight, 30 deg C 2: 87 percent / N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 10 h / Heating 3: 80 percent / 0.1N aq. methanolic sodium hydroxide / 3.5 h / 100 °C View Scheme

1: 87 percent / N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 10 h / Heating 2: 80 percent / 0.1N aq. methanolic sodium hydroxide / 3.5 h / 100 °C View Scheme

1.1: potassium carbonate; butanone / |Inert atmosphere; |Reflux 2.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / 0 °C / |Inert atmosphere 2.2: 6 h / 20 °C / |Inert atmosphere 3.1: toluene-4-sulfonic acid / toluene / 6 h / |Inert atmosphere; |Dean-Stark; |Reflux 4.1: boron tribromide / dichloromethane / 0 - 20 °C / |Inert atmosphere 4.2: 1 h / 20 °C / |Inert atmosphere View Scheme