N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile in tetrachloromethane; dichloromethane T=75°C; 4 h; Heating / reflux;

1.1: sodium hydroxide / water / 0.5 h / 80 - 90 °C 1.2: pH 1 2.1: 5 palladium on charcoal; hydrogen / ethanol / 50 °C / 2585.81 Torr 3.1: triethylamine; trichlorophosphate / dichloromethane / 8 h / 40 °C / |Reflux 4.1: 2,2'-azo-bisisobutyronitrile; N-bromosuccinmide / dichloromethane / 12 h / |Inert atmosphere; |Reflux View Scheme

1: triethylamine; trichlorophosphate / dichloromethane / 8 h / 40 °C / |Reflux 2: 2,2'-azo-bisisobutyronitrile; N-bromosuccinmide / dichloromethane / 12 h / |Inert atmosphere; |Reflux View Scheme

1: With lead; iodine; zinc in tetrahydrofuran T=5 - 25°C; Reformatsky Reaction; Inert atmosphere; 2: With hydrogenchloride in isopropyl alcohol T=25°C;

1: With zinc(II) chloride; zinc in tetrahydrofuran T=-5 - 5°C; 1 h; 2: With ammonium formate; zinc in methanol T=20°C; 16 h; 3: Heating / reflux; Product distribution / selectivity;

1.1: lead; zinc; bromine / dichloromethane; tetrahydrofuran / 30 - 50 °C 1.2: 4 h / 20 - 25 °C 2.1: sodium hydroxide / water; methanol / 20 - 25 °C / pH 8 - 9 2.2: 55 - 60 °C 2.3: 1 h / 40 - 45 °C 3.1: sodium hydroxide / dichloromethane; water / 15 - 25 °C / pH 10 - 11 View Scheme

1: With lead; iodine; zinc in tetrahydrofuran T=5 - 25°C; Reformatsky Reaction; Inert atmosphere; 2: With hydrogenchloride in isopropyl alcohol T=25°C;