1: 54 percent / K2CO3 / acetone / Heating 2: 52 percent / K2CO3 / acetone / Heating View Scheme

potassium carbonate in cyclohexanone 6 h; Heating;

1: 1.) NaH / 1.) DME, 25 deg C, 2.) DME, reflux, 26 h 2: aq. H2SO4 / acetic acid / 20 h / Heating 3: p-toluenesulfonic acid / benzene / 7 h / Heating 4: 28.6 g / p-toluenesulfonic acid / benzene / Heating 5: Br2, CaCO3 / CHCl3; CCl4 / 0.5 h / 5 °C 6: 72 percent / LiBr2, Li2CO3 / dimethylformamide / 0.5 h / Heating 7: 100 percent / N-bromosuccinimide, 2,2-azadiisobutyronitrile / CCl4 / 5 h / Heating 8: 62 percent / H2O / dioxane / 2.5 h / Heating View Scheme

1: 1.) NaH / 1.) DME, 25 deg C, 2.) DME, reflux, 26 h 2: aq. H2SO4 / acetic acid / 20 h / Heating 3: p-toluenesulfonic acid / benzene / 7 h / Heating 4: 28.6 g / p-toluenesulfonic acid / benzene / Heating 5: Br2, CaCO3 / CHCl3; CCl4 / 0.5 h / 5 °C 6: 72 percent / LiBr2, Li2CO3 / dimethylformamide / 0.5 h / Heating 7: 100 percent / N-bromosuccinimide, 2,2-azadiisobutyronitrile / CCl4 / 5 h / Heating 8: 62 percent / H2O / dioxane / 2.5 h / Heating 9: 72 percent / conc. HCl / 4 h / Ambient temperature View Scheme