1: 85 percent / Pd(PPh3)4; 2 M aq. Na2CO3 / 1,2-dimethoxy-ethane; ethanol / 12 h / Heating 2: 92 percent / LDA / tetrahydrofuran / 10 h / 20 °C 3: 95 percent / BBr3 / CH2Cl2 / 12 h / -78 - 20 °C View Scheme

1: 92 percent / LDA / tetrahydrofuran / 10 h / 20 °C 2: 95 percent / BBr3 / CH2Cl2 / 12 h / -78 - 20 °C View Scheme

1: n-Pentyl nitrite / acetic acid / 1 h / 0 °C / |Inert atmosphere 2: potassium iodide / acetic acid; water / 3 h / 20 °C / |Inert atmosphere 3: copper(l) iodide; potassium phosphate / N,N-dimethyl-formamide / 0.5 h / 160 °C / |Inert atmosphere; |Microwave irradiation 4: boron tribromide / dichloromethane / 24 h / -78 - 20 °C / |Inert atmosphere View Scheme

1: copper(l) iodide; potassium phosphate / N,N-dimethyl-formamide / 0.5 h / 160 °C / |Inert atmosphere; |Microwave irradiation 2: boron tribromide / dichloromethane / 24 h / -78 - 20 °C / |Inert atmosphere View Scheme

sulfuric acid

1: 1-hydroxy-9H-fluoren-9-one With sodium hydride in N,N-dimethyl-formamide T=0 - 20°C; 0.5 h; 2: methyl iodide in N,N-dimethyl-formamide T=20°C; 2 h;