1: oxalyl chloride / CH2Cl2 / 18 h / 0 deg C -> room temp. 2: CH2Cl2 / 18 h / Ambient temperature 3: thionyl chloride / 0.5 h / Ambient temperature 4: 20percent aq. NaOH 5: 84 percent / tetrahydrofuran / 1.5 h / -15 - 0 °C 6: 67 percent / aq. HCl / 36 h / Heating View Scheme

1: 87 percent / SOCl2, DMF / 4 h / Heating 2: CH2Cl2 / 24 h / 25 °C 3: SOCl2 / benzene / 2 h / 25 °C 4: 1.) Mg / 2.) dichlorobis(triphenylphosphine)nickel / 1.) THF, 2.5 h reflux, 2.) benzene, cautiously addition of catalyst, 30 min reflux 5: 2.) 20percent aqueous NaOH / 1.) 9 h, 2.) MeOH, reflux, 40 h 6: SOCl2, DMF / 0.5 h / Heating 7: NaN3 / acetone; H2O / 0.5 h / 25 °C 8: benzene / 2 h / Heating 9: 1.) aqueous 50 percent KOH / 1.) benzene, 2.) reflux, 1 h, 10: 1.) NaNO2/HCl, 2.) H3PO2 / 1.) water, 20 min, 0 deg C, 2.) 45 min, 4 deg C View Scheme

1: 87 percent / SOCl2, DMF / 4 h / Heating 2: CH2Cl2 / 24 h / 25 °C 3: SOCl2 / benzene / 2 h / 25 °C 4: 1.) Mg / 2.) dichlorobis(triphenylphosphine)nickel / 1.) Et2O, 2.) benzene, 5 min reflux 5: 2.) aqueous 20percent NaOH / 1.) 24 h, 2.) MeOH, reflux 6: SOCl2, DMF / 0.5 h / Heating View Scheme

1: thionyl chloride 2: aqueous ammonia 3: phosphorus (V)-chloride 4: diethyl ether / anschliessendes Behandeln mit wss.NH4Cl und Erhitzen des Reaktionsprodukts mit wss.HCl View Scheme

1: oxalyl chloride / CH2Cl2 / 18 h / 0 deg C -> room temp. 2: CH2Cl2 / 18 h / Ambient temperature 3: thionyl chloride / 0.5 h / Ambient temperature 4: 20percent aq. NaOH 5: 84 percent / tetrahydrofuran; diethyl ether / 1.5 h / -15 - 0 °C 6: 88 percent / aq. HCl / 20 h / Heating View Scheme

thionyl chloride 2 h; Heating / reflux;

Pd(OTf)2; silver carbonate in dimethyl sulfoxide; N,N-dimethyl-formamide T=100°C;

1: thionyl chloride 2: aqueous ammonia 3: phosphorus (V)-chloride View Scheme