1: 92 percent / PBr3 / CHCl3 2: 73 percent / NaOEt / diethyl ether / 24 h / Ambient temperature 3: 61 percent / KOH / ethanol; H2O / 6 h / Heating 4: 79 percent / urea / xylene / Heating 5: 71 percent / sodium bis(2-methoxyethoxy)aluminum hydride / benzene / 2 h / Heating View Scheme

hydrogen; palladium on activated charcoal in ethanol

tin(IV) chloride in dichloromethane T=20°C; Friedel Crafts alkylation; 2 h; regioselective reaction;

1: 60 percent / AlCl3 / nitrobenzene 2: 94 percent / H2 / 10percent Pd/C / ethanol View Scheme