isopropylmagnesium chloride in tetrahydrofuran T=0°C; 2 h;

2,2,6,6-tetramethylpiperidinyl-lithium T=-78°C; 6 h; Large scale reaction;

triethylamine tris(hydrogen fluoride) in N,N-dimethyl-formamide T=23°C; 48 h; Inert atmosphere;

potassium permanganate in water Heating;

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

1: 74 percent / copper(I) iodide; potassium fluoride / 1-methyl-pyrrolidin-2-one / 25 °C 2: 84 percent / isopropylmagnesium chloride / tetrahydrofuran / 2 h / 0 °C View Scheme

1: 88 percent / NaNO2, Br2, 48percent HBr / 5 °C 2: 48 percent / Cu, HMPA / 4 h / 112 - 130 °C / autoclave 3: 34 percent / KMnO4 / H2O / Heating View Scheme

1: 48 percent / Cu, HMPA / 4 h / 112 - 130 °C / autoclave 2: 34 percent / KMnO4 / H2O / Heating View Scheme