acetic acid; sodium nitrite; Copper(I)chloride in hydrogenchloride

1: 5-bromo-1,2,3-trichlorobenzene With n-butyllithium in tetrahydrofuran; hexane T=-75°C; 0.25 h; 2: carbon dioxide in tetrahydrofuran; hexane

(2,2'-bipyridine-N,N')dichloronickel; zinc in water; N,N-dimethyl-formamide T=70°C; 4 h;

1.1: diisopropylamine / hexane; tetrahydrofuran / 2 h / -75 °C 1.2: butyllithium / tetrahydrofuran; diethyl ether; hexane / 0.25 h / -100 °C 1.3: 49 percent / butyllithium / hexane; diethyl ether / 0.25 h / -100 °C 2.1: butyllithium / hexane; tetrahydrofuran / 0.25 h / -75 °C 2.2: hexane; tetrahydrofuran View Scheme

1.1: diisopropylamine; butyllithium / hexane; tetrahydrofuran / 2 h / -75 °C 1.2: 89 percent / hexane; tetrahydrofuran 2.1: 96 percent / bromine / CCl4 / 12 h / Heating 3.1: diisopropylamine / hexane; tetrahydrofuran / 2 h / -75 °C 3.2: butyllithium / tetrahydrofuran; diethyl ether; hexane / 0.25 h / -100 °C 3.3: 49 percent / butyllithium / hexane; diethyl ether / 0.25 h / -100 °C 4.1: butyllithium / hexane; tetrahydrofuran / 0.25 h / -75 °C 4.2: hexane; tetrahydrofuran View Scheme

1.1: 96 percent / bromine / CCl4 / 12 h / Heating 2.1: diisopropylamine / hexane; tetrahydrofuran / 2 h / -75 °C 2.2: butyllithium / tetrahydrofuran; diethyl ether; hexane / 0.25 h / -100 °C 2.3: 49 percent / butyllithium / hexane; diethyl ether / 0.25 h / -100 °C 3.1: butyllithium / hexane; tetrahydrofuran / 0.25 h / -75 °C 3.2: hexane; tetrahydrofuran View Scheme

1.1: diisopropylamine; butyllithium / hexane; tetrahydrofuran / 2 h / -75 °C 1.2: 89 percent / hexane; tetrahydrofuran 2.1: diisopropylamine; butyllithium / hexane; tetrahydrofuran / 2 h / -75 °C 2.2: 89 percent / hexane; tetrahydrofuran 3.1: 96 percent / bromine / CCl4 / 12 h / Heating 4.1: diisopropylamine / hexane; tetrahydrofuran / 2 h / -75 °C 4.2: butyllithium / tetrahydrofuran; diethyl ether; hexane / 0.25 h / -100 °C 4.3: 49 percent / butyllithium / hexane; diethyl ether / 0.25 h / -100 °C 5.1: butyllithium / hexane; tetrahydrofuran / 0.25 h / -75 °C 5.2: hexane; tetrahydrofuran View Scheme

hydrogenchloride T=200 - 210°C;

alkaline potassium permanganate

iodine durch Chlorierung und Verseifen mit Natronlauge;