1: 1.) NaH / 2.) 3 h, 90 deg C 2: 1.) Mg / 2.) dichlorobis(triphenylphosphine)nickel / 1.) Et2O <1,2-dibromoethane>, reflux, 1.5 h, 2.) benzene, 25 deg C, 53 h 3: 75 percent / 4 N HCl / 24 h / Heating View Scheme

1: 1.) NaH / 2.) 3 h, 90 deg C 2: 1.) Mg / 1.) Et2O <dibromoethane>, benzene, reflux, 2.) reflux, 3.25 h 3: 2.) aqueous 20 percent NaOH / 1.) 12 h, 25 deg C, 2.) MeOH, 24 h, reflux 4: BH3*THF / tetrahydrofuran / 1.a) 10 min, 0 deg C, b) 1 h, 25 deg C, 2.) THF/H2O = 2:1, 15 min, 25 deg C View Scheme

1: 84 percent / tetrahydrofuran / 1.5 h / -15 - 0 °C 2: 67 percent / aq. HCl / 36 h / Heating View Scheme

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

1: 84 percent / tetrahydrofuran; diethyl ether / 1.5 h / -15 - 0 °C 2: 88 percent / aq. HCl / 20 h / Heating View Scheme