hydrogenchloride; iron in ethanol 2 h; Heating;

1: 77 percent / potassium t-butoxide / dimethylsulfoxide; 2-methyl-propan-2-ol / r.t., 5min. then 70-75 degC, 10min. 2: 74 percent / SOCl2 / pyridine / r.t., 1h then 80 degC, 15min. 3: 73 percent / conc. HCl, Fe (filings) / ethanol / 2 h / Heating View Scheme

1: 74 percent / SOCl2 / pyridine / r.t., 1h then 80 degC, 15min. 2: 73 percent / conc. HCl, Fe (filings) / ethanol / 2 h / Heating View Scheme

triethylsilane; trifluoroacetic acid T=50°C; Inert atmosphere;

palladium on activated charcoal in toluene 12 h; Heating;