hydrogen bromide T=135°C; Hydrolysis; decarboxylation; 12 h;

in methanol 3 h; Heating;

1: 98 percent / Et3N / CH2Cl2 / 6 h / 20 °C 2: 85 percent / aq. HCO2H; Pd(OAc)2(PPh3)2; Et3N / dimethylformamide / 1 h / 60 °C View Scheme

1: 85 percent / Et3N; p-acetamidophenylsulfonyl azide / acetonitrile / 0 - 20 °C 2: 86 percent / Rh(OAc)2 / benzene / 14 h / Heating 3: 98 percent / Et3N / CH2Cl2 / 6 h / 20 °C 4: 85 percent / aq. HCO2H; Pd(OAc)2(PPh3)2; Et3N / dimethylformamide / 1 h / 60 °C View Scheme

1: 97 percent / benzene / Heating 2: 1.) cupric acetate, pyridine, 2.) lead tetraacetate / 1.) benzene, RT, 2.) a.) benzene, RT, 2 h, b.) reflux, 1 h 3: 100 percent / methanol / 3 h / Heating View Scheme

in methanol 3 h; Heating;

1: 1.) cupric acetate, pyridine, 2.) lead tetraacetate / 1.) benzene, RT, 2.) a.) benzene, RT, 2 h, b.) reflux, 1 h 2: 100 percent / methanol / 3 h / Heating View Scheme

1: 54 percent / sodium hydride / benzene / 1 h / Heating 2: 100 percent / methanol / 3 h / Heating View Scheme