1: p-TsOH*H2O / methanol / 0.5 h / Ambient temperature 2: K2CO3 / acetone / 8 h / Heating 3: 1.) concd. HCl; 2.) 13 N aq. KOH / 1.) EtOH, 6 h, reflux; 2.) MeOH, 4 h, reflux 4: 47percent aq. HBr, NaNO2 5: 47percent aq. HBr, CuBr / CHCl3 / 0.5 h / 40 °C View Scheme

1: p-TsOH*H2O / methanol / 0.5 h / Ambient temperature 2: K2CO3 / acetone / 8 h / Heating 3: 1.) concd. HCl; 2.) 13 N aq. KOH / 1.) EtOH, 6 h, reflux; 2.) MeOH, 4 h, reflux View Scheme