1: 92 percent / bromine / CCl4 / 75 h / Heating 2: 89 percent / bromotrimethylsilane / various solvent(s) / 50 h / Heating 3: 74 percent / chlorotrimethylsilane; sodium iodide / various solvent(s) / 75 h / Heating View Scheme

bromine in tetrachloromethane 75 h; Heating;

1: 92 percent / bromine / CCl4 / 75 h / Heating 2: 89 percent / bromotrimethylsilane / various solvent(s) / 50 h / Heating 3: 74 percent / chlorotrimethylsilane; sodium iodide / various solvent(s) / 75 h / Heating 4: 74 percent / copper(I) iodide; potassium fluoride / 1-methyl-pyrrolidin-2-one / 25 °C View Scheme

1: 92 percent / bromine / CCl4 / 75 h / Heating 2: 89 percent / bromotrimethylsilane / various solvent(s) / 50 h / Heating 3: 74 percent / chlorotrimethylsilane; sodium iodide / various solvent(s) / 75 h / Heating 4: 74 percent / copper(I) iodide; potassium fluoride / 1-methyl-pyrrolidin-2-one / 25 °C 5: 84 percent / isopropylmagnesium chloride / tetrahydrofuran / 2 h / 0 °C View Scheme

1: 92 percent / bromine / CCl4 / 75 h / Heating 2: 89 percent / bromotrimethylsilane / various solvent(s) / 50 h / Heating View Scheme

copper(l) iodide; tetrabutyl ammonium fluoride; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; para-iodoanisole in N,N-dimethyl-formamide T=20°C; 12 h;

1: alpha-chloropyridine With 2,2,6,6-tetramethyl-piperidine; n-butyllithium in tetrahydrofuran; hexane T=-78°C; 1.5 h; 2: chloro-trimethyl-silane in tetrahydrofuran; hexane T=-78 - -10°C;

1: bromo-3 chloro-2 pyridine With n-butyllithium in tetrahydrofuran T=-78°C; 0.166667 h; 2: chloro-trimethyl-silane in tetrahydrofuran T=-78°C;

1: chloro-2 deuterio-3 pyridine With 2,2,6,6-tetramethyl-piperidine; n-butyllithium in tetrahydrofuran; hexane T=-78°C; 1.5 h; 2: chloro-trimethyl-silane in tetrahydrofuran; hexane T=-78 - -10°C;