2,2'-azo-bisisobutyronitrile; thiophenol in toluene T=80°C; 2 h;

1: With potassium tert-butylate in toluene T=-30 - 20°C; 2: With 2,2'-azo-bisisobutyronitrile; thiophenol in toluene T=80°C; 1 h; Further stages.;

1.1: 93 percent / Br2; AcOH / 5 - 20 °C 2.1: NaH / dimethylsulfoxide; tetrahydrofuran / 60 °C 2.2: 90 percent / 2 h / 60 °C 3.1: 99 percent / thiophenol; AIBN / toluene / 2 h / 80 °C View Scheme

1: (ethyl)-triphenylphosphonium bromide With potassium 2-methyl-2-butoxide in tetrahydrofuran 0.166667 h; Inert atmosphere; 2: 2-bromo-5-methoxy-benzaldehyde in tetrahydrofuran T=20°C; 0.5 h; Cooling with iceInert atmosphere; Overall yield = 97 percent;

1.1: N-bromosuccinmide / acetonitrile / 20 °C 2.1: pyridinium chlorochromate / dichloromethane / 20 °C 3.1: potassium 2-methyl-2-butoxide / tetrahydrofuran / 0.17 h / |Inert atmosphere 3.2: 0.5 h / 20 °C / |Cooling with ice; |Inert atmosphere View Scheme

1.1: pyridinium chlorochromate / dichloromethane / 20 °C 2.1: potassium 2-methyl-2-butoxide / tetrahydrofuran / 0.17 h / |Inert atmosphere 2.2: 0.5 h / 20 °C / |Cooling with ice; |Inert atmosphere View Scheme