hydrogen; Pd catalyst in water; acetic acid

1: 50.9 percent / Et3N / CHCl3; dimethylformamide / Ambient temperature 2: 50.9 percent / hydrogen / Pd catalyst / acetic acid; H2O View Scheme

1: 1.) PCl3, pyridine / 1.) ice-salt cooling, 15 min, then r.t., 30 min, 2.) r.t., overnight 2: 25 percent HBr-AcOH 3: 50.9 percent / Et3N / CHCl3; dimethylformamide / Ambient temperature 4: 50.9 percent / hydrogen / Pd catalyst / acetic acid; H2O View Scheme

1: SOCl2 2: 50.9 percent / Et3N / CHCl3; dimethylformamide / Ambient temperature 3: 50.9 percent / hydrogen / Pd catalyst / acetic acid; H2O View Scheme

1: 25 percent HBr-AcOH 2: 50.9 percent / Et3N / CHCl3; dimethylformamide / Ambient temperature 3: 50.9 percent / hydrogen / Pd catalyst / acetic acid; H2O View Scheme

1: 1.) PCl3, pyridine / 1.) ice-salt cooling, 15 min, then r.t., 30 min, 2.) r.t., overnight 2: 25 percent HBr-AcOH 3: 50.9 percent / Et3N / CHCl3; dimethylformamide / Ambient temperature 4: 50.9 percent / hydrogen / Pd catalyst / acetic acid; H2O View Scheme