potassium hydroxide in ethanol Heating;

1: 94 percent / BF3*Et2O / 2 h / 70 °C 2: 89 percent / KOH / ethanol / 0 - 20 °C 3: 74 percent / iodine / dimethylsulfoxide / 2 h / 190 - 200 °C View Scheme

1.1: boron trifluoride diethyl etherate; acetic acid / 5 h / 80 °C 2.1: pyridine / 15 h / 20 °C / Inert atmosphere 3.1: pyridine; potassium hydroxide / 3 h / 70 °C 3.2: Cooling with ice 4.1: sulfuric acid; acetic acid / 1.5 h / 80 °C 5.1: boron tribromide / dichloromethane / 1.5 h / 0 °C / Inert atmosphere 5.2: 0.5 h / 20 °C / Inert atmosphere 6.1: 10 palladium on activated charcoal; hydrogen / tetrahydrofuran; methanol / 1.5 h / 20 °C View Scheme

1: 94 percent / BF3*Et2O / 2 h / 70 °C 2: 89 percent / KOH / ethanol / 0 - 20 °C 3: 74 percent / iodine / dimethylsulfoxide / 2 h / 190 - 200 °C 4: 58 percent / BBr3 / CH2Cl2 / 13 h / -80 - 20 °C View Scheme

1: 93 percent / BF3*Et2O / acetic acid / 2 h / 70 °C 2: 91 percent / NaH 3: 27 percent / pyridine / CHCl3 / 60 °C View Scheme