1: 1.) SOCl2 / 1.) 30 deg C, 2 h, 2.) CH2Cl2, -10 deg C -5 deg C, 2 h 2: 72 percent Turnov. / cuprous bromide / benzene / 6 h / Heating 3: 1.) HBr, 2.) potassium amide / 1.) CH2Cl2, 0 deg C, 2.) -78 deg C, 1 h View Scheme

1: 86 percent 2: 1.) SOCl2 / 1.) 30 deg C, 2 h, 2.) CH2Cl2, -10 deg C -5 deg C, 2 h 3: 72 percent Turnov. / cuprous bromide / benzene / 6 h / Heating 4: 1.) HBr, 2.) potassium amide / 1.) CH2Cl2, 0 deg C, 2.) -78 deg C, 1 h View Scheme

1: 72 percent Turnov. / cuprous bromide / benzene / 6 h / Heating 2: 1.) HBr, 2.) potassium amide / 1.) CH2Cl2, 0 deg C, 2.) -78 deg C, 1 h View Scheme

hydrogen bromide; KNH2 1.) CH2Cl2, 0 deg C, 2.) -78 deg C, 1 h; Yield given. Multistep reaction;

KNH2; iron nitrate (III) 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C, 1 h; Yield given. Multistep reaction;