trimethylsilyl iodide in tetrachloromethane 14 h; Heating;

1: 1) lithium diisopropylamide / 1) THF, -70 deg C, 1 h, 2) r.t., 2 h 2: HBr(gaseous) / CHCl3 / 6 h 3: 74 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / benzene / 24 h / Heating 4: 82 percent / trimethylsilyl iodide / CCl4 / 14 h / Heating View Scheme

1: HBr(gaseous) / CHCl3 / 6 h 2: 74 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / benzene / 24 h / Heating 3: 82 percent / trimethylsilyl iodide / CCl4 / 14 h / Heating View Scheme

1: 74 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / benzene / 24 h / Heating 2: 82 percent / trimethylsilyl iodide / CCl4 / 14 h / Heating View Scheme

sodium hydroxide in ethanol; water 15 h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

(i) nBuLi, (ii) /BRN= 505934/; Multistep reaction;