1: 50 percent / cc H2SO4, HNO3 / 1./ 0.5 h. 2./ 1 h. room temp. 2: 1./ cc H2SO4, NaNO2, acetic acid, 2./ CuBr, NaBr, 16percent HBr / 1./ water, 1 h. 3-5 deg C. 3: 38 percent / CuCl, potassium tert-butoxide / 2-methyl-propan-2-ol / 7 h / Heating 4: 100 percent / H2 / Raney-nickel / methanol / 4 h / 52504.2 Torr 5: 76 percent / pyridine / 1./ 3 h. 0 deg C. 2./ room temp. View Scheme

1: 37 percent / HNO3 / 0.25 h / 0 - 5 °C 2: 38 percent / CuCl, potassium tert-butoxide / 2-methyl-propan-2-ol / 7 h / Heating 3: 100 percent / H2 / Raney-nickel / methanol / 4 h / 52504.2 Torr 4: 76 percent / pyridine / 1./ 3 h. 0 deg C. 2./ room temp. View Scheme

1: 1./ cc H2SO4, NaNO2, acetic acid, 2./ CuBr, NaBr, 16percent HBr / 1./ water, 1 h. 3-5 deg C. 2: 38 percent / CuCl, potassium tert-butoxide / 2-methyl-propan-2-ol / 7 h / Heating 3: 100 percent / H2 / Raney-nickel / methanol / 4 h / 52504.2 Torr 4: 76 percent / pyridine / 1./ 3 h. 0 deg C. 2./ room temp. View Scheme

1: 100 percent / 5n HCl / 1.5 h / Heating 2: 1./ cc H2SO4, NaNO2, acetic acid, 2./ CuBr, NaBr, 16percent HBr / 1./ water, 1 h. 3-5 deg C. 3: 38 percent / CuCl, potassium tert-butoxide / 2-methyl-propan-2-ol / 7 h / Heating 4: 100 percent / H2 / Raney-nickel / methanol / 4 h / 52504.2 Torr 5: 76 percent / pyridine / 1./ 3 h. 0 deg C. 2./ room temp. View Scheme

1: 38 percent / CuCl, potassium tert-butoxide / 2-methyl-propan-2-ol / 7 h / Heating 2: 100 percent / H2 / Raney-nickel / methanol / 4 h / 52504.2 Torr 3: 76 percent / pyridine / 1./ 3 h. 0 deg C. 2./ room temp. View Scheme

1: 75 percent / HNO3 / acetic acid / 2 h / Ambient temperature 2: 100 percent / 5n HCl / 1.5 h / Heating 3: 1./ cc H2SO4, NaNO2, acetic acid, 2./ CuBr, NaBr, 16percent HBr / 1./ water, 1 h. 3-5 deg C. 4: 38 percent / CuCl, potassium tert-butoxide / 2-methyl-propan-2-ol / 7 h / Heating 5: 100 percent / H2 / Raney-nickel / methanol / 4 h / 52504.2 Torr 6: 76 percent / pyridine / 1./ 3 h. 0 deg C. 2./ room temp. View Scheme

1: 100 percent / H2 / Raney-nickel / methanol / 4 h / 52504.2 Torr 2: 76 percent / pyridine / 1./ 3 h. 0 deg C. 2./ room temp. View Scheme

pyridine 1./ 3 h. 0 deg C. 2./ room temp.;