in diethyl ether 30 h; from -78 deg C to room temp.;

1: 72 percent / KF / dimethylformamide / 12 h / 120 - 130 °C 2: 1.) SOCl2 / 1.) 80 deg C, 2 h, 2.) CH2Cl2, -10 deg C -5 deg C, water, then 2 h, 0 deg C 3: 71 percent / cuprous bromide / benzene / 6 h / Heating 4: 1.) HBr, 2.) potassium amide, ferric nitrate / 1.) CH2Cl2, 0 deg C, 2.) -78 deg C, 1 h View Scheme

1: 1.) SOCl2 / 1.) 80 deg C, 2 h, 2.) CH2Cl2, -10 deg C -5 deg C, water, then 2 h, 0 deg C 2: 71 percent / cuprous bromide / benzene / 6 h / Heating 3: 1.) HBr, 2.) potassium amide, ferric nitrate / 1.) CH2Cl2, 0 deg C, 2.) -78 deg C, 1 h View Scheme

1: 72 percent / KF / dimethylformamide / 12 h / 120 - 130 °C 2: 1.) SOCl2 / 1.) 80 deg C, 2 h, 2.) CH2Cl2, -10 deg C -5 deg C, water, then 2 h, 0 deg C 3: 71 percent / cuprous bromide / benzene / 6 h / Heating 4: 1.) HBr, 2.) potassium amide, ferric nitrate / 1.) CH2Cl2, 0 deg C, 2.) -78 deg C, 1 h View Scheme

naphthalene; di-tert-butyl peroxide; copper(ll) bromide T=120 - 130°C; 4 h; in photolytic reaction, too;

copper(I) bromide in benzene 6 h; Heating;

1: 72 percent / iodine, sodium hydroxide, potasium iodide, sodium sulphide / methanol 2: SOCl2 / benzene / 4 h / Heating 3: CH2Cl2 / 2 h / Ambient temperature 4: 57 percent / pyridine, bromine / CH2Cl2 / from -78 deg C to room temp. 5: 80 percent / sulphuryl chloride / CCl4 / Ambient temperature 6: 89 percent / diethyl ether / 30 h / from -78 deg C to room temp. View Scheme

1: CH2Cl2 / 2 h / Ambient temperature 2: 57 percent / pyridine, bromine / CH2Cl2 / from -78 deg C to room temp. 3: 80 percent / sulphuryl chloride / CCl4 / Ambient temperature 4: 89 percent / diethyl ether / 30 h / from -78 deg C to room temp. View Scheme

1: SOCl2 / benzene / 4 h / Heating 2: CH2Cl2 / 2 h / Ambient temperature 3: 57 percent / pyridine, bromine / CH2Cl2 / from -78 deg C to room temp. 4: 80 percent / sulphuryl chloride / CCl4 / Ambient temperature 5: 89 percent / diethyl ether / 30 h / from -78 deg C to room temp. View Scheme

1: 80 percent / sulphuryl chloride / CCl4 / Ambient temperature 2: 89 percent / diethyl ether / 30 h / from -78 deg C to room temp. View Scheme