sodium hydroxide in ethanol 6 h; Heating;

1.1: 90 percent / HCl; iron / ethanol / 6 h / Heating 2.1: H2SO4; NaNO2 / H2O / 0.5 h / cooling 2.2: 72 percent / KI; copper / H2O / 0.5 h / Heating 3.1: t-BuLi / tetrahydrofuran; pentane / 0.83 h / cooling 3.2: 76 percent / 1,2-dibromoethane / tetrahydrofuran; pentane / 0.5 h / cooling View Scheme

1: 95 percent / acive carbon, N2H4*H2O, FeCl3*6H2O / ethanol / 10 h / Heating 2: 1)NaNO2, H2SO4, acetic acid 2) 48percent HBr, CuBr / 1)r.t., 3 h 2) 70 deg C, 2 h, standing overnight 3: 1)Mg / 1) THF, reflux, 1.5 h 2) reflux, 30 min View Scheme