thionyl chloride; N,N-dimethyl-formamide 0.5 h; Heating;

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

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

2: SOCl2, DMF View Scheme

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