1: With sulfuric acid T=30 - 40°C; Inert atmosphere; 2: With sodium hydroxide in water; isopropyl alcohol T=13 - 33°C; pH=1.5 - 11.2; Product distribution / selectivity;

hydrogenchloride in chloroform

sodium tetrahydroborate; boron trifluoride diethyl etherate in tetrahydrofuran 1) 25 degC, 2 h, 2) reflux, 2 h;

1: 62 percent / bromine / acetic acid / 4 h / Ambient temperature 2: 1) BuLi, 2) nitrobenzene / 1) THF, hexane, -60 deg C, 45 min, 2) THF, hexane, -196 to -60 deg C and 3.5 h at -60 deg C View Scheme

1: 92 percent / CHCl3 / 2 h / 60 °C 2: 30 percent / Zn / H2O; acetic acid / 3 h / 60 °C View Scheme

1: 62 percent / bromine / acetic acid / 4 h / Ambient temperature 2: 1) BuLi, 2) nitrobenzene / 1) THF, hexane, -60 deg C, 45 min, 2) THF, hexane, -196 to -60 deg C and 3.5 h at -60 deg C 3: 1) ClCOOEt, 2) 48percent aq. HBr / 1) toluene, reflux, 2 h, 2) 5 h, reflux View Scheme

1: 92 percent / CHCl3 / 2 h / 60 °C 2: 30 percent / Zn / H2O; acetic acid / 3 h / 60 °C 3: 31 percent / C(2)H3I; NaHCO3 / methanol / 3 h / 30 °C View Scheme