hydrogenchloride; triethylamine in dimethyl sulfoxide; benzene

in dimethyl sulfoxide T=20°C; 2 h;

dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine; bis(η3-allyl-μ-chloropalladium(II)) in 1,3,5-trimethyl-benzene T=20 - 140°C; 5.16667 h; Inert atmosphereSealed tube; chemoselective reaction;

1: 97 percent / thionyl chloride / toluene / 0.5 h / 20 °C 2: 89 percent / dimethylsulfoxide / 2 h / 20 °C View Scheme

thionyl chloride 1.) dichloromethane, dimethylsulfoxide; Yield given. Multistep reaction;

1.1: toluene / 0.67 h / Reflux 1.2: Reflux 2.1: hydrogenchloride; water; acetic acid / 40 °C / Reflux 2.2: 0.17 h / 0 - 5 °C / pH 7 - 7.2 3.1: sulfuric acid / dichloromethane; water 3.2: 18 - 20 °C 3.3: 0.67 h / 25 - 30 °C / pH 6.95 - 7.1 View Scheme

1.1: hydrogenchloride; sodium methylate / toluene; water / 25 - 30 °C / pH 5.2-6.2 / |Reflux 1.2: 40 - 50 °C / |Reflux 2.1: potassium tert-butylate / isopropyl alcohol / 5 - 8 °C 3.1: sulfuric acid; sodium tungstate; Aliquatreg; 336 / isopropyl alcohol; dichloromethane; water / 10 - 28 °C 3.2: 8 - 30 °C / pH 6.8 - 7 View Scheme

1: With potassium hydroxide; water 8 h; Reflux; 2: With hydrogenchloride; water T=20°C;