1: 85 percent / Br2, Na2CO3 / CCl4 / 0.25 h / 0 °C 2: 64 percent / 50percent NaOH, 40percent Bu4NOH / 4 h / 100 °C 3: 62 percent / hexamethyldisilazane, ISiMe3 / CCl4 / 1) 0 deg C, 2 h, 2) RT, 15 h 4: 1) t-BuLi / 1) ether, -70 deg C, 90 min, 2a) ether, -70 deg C, 1 h, 2b) -30 deg C, 1.5 h 5: 1) t-BuLi / 1) ether, -70 deg C, 90 min, 2a) ether, -70 deg C, 1 h, 2b) -30 deg C, 1.5 h View Scheme

1: 85 percent / Br2, Na2CO3 / CCl4 / 0.25 h / 0 °C 2: 64 percent / 50percent NaOH, 40percent Bu4NOH / 4 h / 100 °C 3: 62 percent / hexamethyldisilazane, ISiMe3 / CCl4 / 1) 0 deg C, 2 h, 2) RT, 15 h 4: 1) t-BuLi / 1) ether, -70 deg C, 90 min, 2a) ether, -70 deg C, 1 h, 2b) -30 deg C, 1.5 h 5: 1) t-BuLi / 1) ether, -70 deg C, 90 min, 2a) ether, -70 deg C, 1 h, 2b) -30 deg C, 1.5 h View Scheme

1: 85 percent / Br2, Na2CO3 / CCl4 / 0.25 h / 0 °C 2: 64 percent / 50percent NaOH, 40percent Bu4NOH / 4 h / 100 °C 3: 62 percent / hexamethyldisilazane, ISiMe3 / CCl4 / 1) 0 deg C, 2 h, 2) RT, 15 h 4: 1) t-BuLi / 1) ether, -70 deg C, 90 min, 2a) ether, -70 deg C, 1 h, 2b) -30 deg C, 1.5 h 5: 1) t-BuLi / 1) ether, -70 deg C, 90 min, 2a) ether, -70 deg C, 1 h, 2b) -30 deg C, 1.5 h View Scheme

N,N,N',N,-tetramethylethylenediamine; iron(III) chloride in tetrahydrofuran T=0°C; 0.5 h;

diethyl ether

in tetrahydrofuran Heating;

magnesium 1) THF, 2 h, RT, 2) THF, RT, 20 h; Yield given. Multistep reaction;

magnesium

zinc 1.) THF, 2.) THF; Yield given. Multistep reaction;

Reagiert die Magnesiumverbindung;