1: 1.) CH3Li, LiBr, 2.) tert-BuLi / 1.) diethyl ether, 50 min, 2.) diethyl ether/pentane, -78 deg C, 1 h, 3.) -78 to 0 deg C, 30 min 2: conc. HCl / methanol / 4.5 h / Heating 3: 61 percent / Jones reagent / acetone / 5 h / -30 °C View Scheme

With  bromine; tert-butylamine in  toluene T=-78 - 5°C; 4 h;   

Multi-step reaction with 5 steps 1: triethylamine / 4-(dimethylamino)pyridine / CH2Cl2 / 20 h / Ambient temperature2: K2CO3 / methanol / 24 h / Ambient temperature3: 1.) n-BuLi, 2.) methanesulfonyl chloride, 3.) Li2CuCl4 / 1.) THF/n-hexane, -78 deg C, 35 min, 2.) -78 deg C, 2 h, 3.) THF/n-hexane/diethyl ether -78 deg C to room temp. over 2.5 h then 25 deg C, 3 h4: 73 percent / benzene / 14 h / 120 °C / in a sealed tube5: 85 percent / Br2, tert butylamine / toluene / 4 h / -78 - 5 °C  

Multi-step reaction with 4 steps 1: K2CO3 / methanol / 24 h / Ambient temperature2: 1.) n-BuLi, 2.) methanesulfonyl chloride, 3.) Li2CuCl4 / 1.) THF/n-hexane, -78 deg C, 35 min, 2.) -78 deg C, 2 h, 3.) THF/n-hexane/diethyl ether -78 deg C to room temp. over 2.5 h then 25 deg C, 3 h3: 73 percent / benzene / 14 h / 120 °C / in a sealed tube4: 85 percent / Br2, tert butylamine / toluene / 4 h / -78 - 5 °C  

Multi-step reaction with 3 steps 1: 1.) n-BuLi, 2.) methanesulfonyl chloride, 3.) Li2CuCl4 / 1.) THF/n-hexane, -78 deg C, 35 min, 2.) -78 deg C, 2 h, 3.) THF/n-hexane/diethyl ether -78 deg C to room temp. over 2.5 h then 25 deg C, 3 h2: 73 percent / benzene / 14 h / 120 °C / in a sealed tube3: 85 percent / Br2, tert butylamine / toluene / 4 h / -78 - 5 °C  

Multi-step reaction with 2 steps 1: 73 percent / benzene / 14 h / 120 °C / in a sealed tube2: 85 percent / Br2, tert butylamine / toluene / 4 h / -78 - 5 °C