1: 1-bromo-5-chloro-pentane With magnesium 2: oxalic acid diethyl ester in tetrahydrofuran T=-15°C; 3: With hydrogenchloride in tetrahydrofuran Product distribution / selectivity;

1: in tetrahydrofuran T=-30 - 5°C; 2: With hydrogenchloride in tetrahydrofuran Product distribution / selectivity;

sodium hypochlorite; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; sodium hydrogencarbonate; potassium bromide in dichloromethane; water T=-1 - 5°C; 2.5 h; Product distribution / selectivity;

1: With toluene-4-sulfonic acid in dichloromethane T=20°C; 2: With sodium hydroxide; water in dichloromethane pH=8 - 9; Product distribution / selectivity;

1.1: sodium hydrogencarbonate; sodium hypochlorite; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical / potassium bromide / dichloromethane; water / 0.83 h / -5 - 10 °C 2.1: sodium hydrogensulfite / water / 2.67 h / 5 °C 2.2: 12 h / 5 - 20 °C 3.1: hydrogenchloride; water / 140 h / 25 °C 4.1: sulfuric acid / Reflux 5.1: sodium hydrogencarbonate; sodium hypochlorite; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical / potassium bromide / dichloromethane; water / 2.5 h / -1 - 5 °C View Scheme

1.1: sodium hydrogensulfite / water / 2.67 h / 5 °C 1.2: 12 h / 5 - 20 °C 2.1: hydrogenchloride; water / 140 h / 25 °C 3.1: sulfuric acid / Reflux 4.1: sodium hydrogencarbonate; sodium hypochlorite; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical / potassium bromide / dichloromethane; water / 2.5 h / -1 - 5 °C View Scheme

1: sulfuric acid / Reflux 2: sodium hydrogencarbonate; sodium hypochlorite; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical / potassium bromide / dichloromethane; water / 2.5 h / -1 - 5 °C View Scheme

1: hydrogenchloride; water / 140 h / 25 °C 2: sulfuric acid / Reflux 3: sodium hydrogencarbonate; sodium hypochlorite; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical / potassium bromide / dichloromethane; water / 2.5 h / -1 - 5 °C View Scheme

1.1: toluene-4-sulfonic acid / toluene / 20 h / Reflux 1.2: 8 h / 5 - 30 °C 2.1: sodium hydroxide / methanol / 60 - 65 °C 2.2: pH 7 View Scheme