water; hydrogen bromide

1: 59 percent / Cu / 1.) 220 deg C, 2 h, 2.) 250 deg C, 1 h 2: 69 percent / LiBH4 / tetrahydrofuran / Heating 3: 93 percent / HBr, H2O View Scheme

1: 1.) NaNO2, HCl, 2.) KI / 1.) H2O, -5 deg C, 2.) H2O, toluene, r.t., 12 h; reflux, 1 h 2: 59 percent / Cu / 1.) 220 deg C, 2 h, 2.) 250 deg C, 1 h 3: 69 percent / LiBH4 / tetrahydrofuran / Heating 4: 93 percent / HBr, H2O View Scheme

1: 69 percent / LiBH4 / tetrahydrofuran / Heating 2: 93 percent / HBr, H2O View Scheme