water; ammonium formate; palladium 10 on activated carbon in acetic acid 1 h; Heating / reflux;

boron tribromide in dichloromethane 1.) -78 deg C, 5 h, 2.) RT, 8 h;

1: 85 percent / H2, H2SO4 / 5percent Pd/C / ethyl acetate / 10 h / 2585.7 Torr / Ambient temperature 2: 89 percent / BBr3 / CH2Cl2 / 1.) -78 deg C, 5 h, 2.) RT, 8 h View Scheme

1: 1.) t-BuLi/TMEDA / 1.) ether, hexane, -78 deg C, 5 h, 2.) 15 min 2: 85 percent / H2, H2SO4 / 5percent Pd/C / ethyl acetate / 10 h / 2585.7 Torr / Ambient temperature 3: 89 percent / BBr3 / CH2Cl2 / 1.) -78 deg C, 5 h, 2.) RT, 8 h View Scheme