ammonia in dichloromethane T=-78°C; 12 h;

1: liq. NH3 / CH2Cl2 / 18 h / Ambient temperature 2: 77 percent / tert-butyl hypochlorite, Et3N / ethanol; 2-methyl-propan-2-ol / 2 h / Ambient temperature 3: 1.) thallium(III) trifluoroacetate, 2.) PdCl2, LiCl, MgO / 1.) TFA, r.t., 24 h, 2.) r.t., 43 h View Scheme

1: liq. NH3 / CH2Cl2 / 18 h / Ambient temperature 2: 77 percent / tert-butyl hypochlorite, Et3N / ethanol; 2-methyl-propan-2-ol / 2 h / Ambient temperature 3: 1.) thallium(III) trifluoroacetate, 2.) PdCl2, LiCl, MgO / 1.) TFA, r.t., 24 h, 2.) r.t., 43 h 4: 98 percent / BBr3 / CH2Cl2 / 0.5 h / 0 °C View Scheme

1: liq. NH3 / CH2Cl2 / 18 h / Ambient temperature 2: 77 percent / tert-butyl hypochlorite, Et3N / ethanol; 2-methyl-propan-2-ol / 2 h / Ambient temperature View Scheme