1: With boron tribromide in dichloromethane T=-78°C; 3 h; Inert atmosphere; 2: With water in dichloromethane Inert atmosphere;

toluene-4-sulfonic acid in benzene 2 h; Reflux;

potassium hydroxide in methanol T=-20°C; 6.5 h;

potassium carbonate in methanol T=0°C;

1.1: NaH; EtOH / 1 h / 0 °C 1.2: 76 percent / K2CO3; MeI / acetone / 2.5 h / Heating 2.1: 51 percent / NaOH / ethanol; H2O / 5.5 h / Heating 3.1: 91 percent / pyridine / CH2Cl2 / 0 - 20 °C 4.1: 98 percent / Et3N; formic acid; Ph3P / palladium(II) acetate / 3 h / 50 °C 5.1: 98 percent / palldium(II) chloride; conc. HCl / 2-methyl-propan-2-ol / 0.67 h / Heating 6.1: 93 percent / palldium(II) chloride; conc. HCl / 4 h / Heating View Scheme

hydrogenchloride; palladium dichloride 4 h; Heating;

1: 91 percent / pyridine / CH2Cl2 / 0 - 20 °C 2: 98 percent / Et3N; formic acid; Ph3P / palladium(II) acetate / 3 h / 50 °C 3: 98 percent / palldium(II) chloride; conc. HCl / 2-methyl-propan-2-ol / 0.67 h / Heating 4: 93 percent / palldium(II) chloride; conc. HCl / 4 h / Heating View Scheme

1: 51 percent / NaOH / ethanol; H2O / 5.5 h / Heating 2: 91 percent / pyridine / CH2Cl2 / 0 - 20 °C 3: 98 percent / Et3N; formic acid; Ph3P / palladium(II) acetate / 3 h / 50 °C 4: 98 percent / palldium(II) chloride; conc. HCl / 2-methyl-propan-2-ol / 0.67 h / Heating 5: 93 percent / palldium(II) chloride; conc. HCl / 4 h / Heating View Scheme

1: 98 percent / Et3N; formic acid; Ph3P / palladium(II) acetate / 3 h / 50 °C 2: 98 percent / palldium(II) chloride; conc. HCl / 2-methyl-propan-2-ol / 0.67 h / Heating 3: 93 percent / palldium(II) chloride; conc. HCl / 4 h / Heating View Scheme

trimethylsilyl iodide