P2O5; methanesulfonic acid

AlCl3, aluminium chloride in dichloromethane T=0 - 20°C; 2 h;

hydrogen bromide; iron; sodium hydrogencarbonate in dichloromethane; water; bromine

phosphoric acid; sulfuric acid in water T=40 - 90°C; Inert atmosphere;

1: sodium chloride / 0 - 25 °C / |Inert atmosphere 2: iodine; phosphorous; sulfuric acid / water / 6 h / 110 - 140 °C / |Inert atmosphere 3: phosphoric acid; sulfuric acid / water / 40 - 90 °C / |Inert atmosphere View Scheme

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 - 20 °C 2.1: potassium carbonate; copper(l) iodide; triphenylphosphine; palladium 10 on activated carbon / ethylene glycol dimethyl ether; water / 0.5 h / 20 °C 2.2: 5 h / 80 °C 3.1: sodium hydride / toluene; mineral oil / |Reflux 4.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 3 h / 50 °C / |Inert atmosphere 5.1: phosphorus trichoride / N,N-dimethyl-formamide / 1 h / -20 °C View Scheme

1: 6-bromo-4,4-dimethyl-3,4-dihydro-2H-1-benzothiopyran With n-butyllithium in tetrahydrofuran T=-78°C; 0.166667 h; 2: N,N-dimethyl-formamide in tetrahydrofuran T=20°C;

n-butyllithium in tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 - 20 °C 2.1: potassium carbonate; copper(l) iodide; triphenylphosphine; palladium 10 on activated carbon / ethylene glycol dimethyl ether; water / 0.5 h / 20 °C 2.2: 5 h / 80 °C View Scheme

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 - 20 °C 2.1: potassium carbonate; copper(l) iodide; triphenylphosphine; palladium 10 on activated carbon / ethylene glycol dimethyl ether; water / 0.5 h / 20 °C 2.2: 5 h / 80 °C 3.1: sodium hydride / toluene; mineral oil / |Reflux View Scheme