1: SOCl2, DMF / 3 h / Heating 2: AlCl3 / CCl4 / 15 h / 85 °C 3: 51.4 percent / dibenzoyl peroxide, NBS / benzene / 24 h / Heating 4: 1.) NaH / 1.) DMF, RT, 20 min, 2.) DMF, RT, 1 h View Scheme

silver carbonate in dimethyl sulfoxide T=120°C; 16 h; Sealed tube;

1: N-chloro-succinimide; palladium diacetate; sodium peroxodisulphate; trifluorormethanesulfonic acid / 1,2-dichloro-ethane / 6 h / 60 °C / |Sealed tube 2: potassium hydroxide / methanol / 12 h / |Sealed tube; |Reflux View Scheme

1: N-chloro-succinimide; palladium diacetate; sodium peroxodisulphate; trifluorormethanesulfonic acid / 1,2-dichloro-ethane / 4 h / 70 °C / |Sealed tube 2: N-chloro-succinimide; palladium diacetate; sodium peroxodisulphate; trifluorormethanesulfonic acid / 1,2-dichloro-ethane / 6 h / 60 °C / |Sealed tube 3: potassium hydroxide / methanol / 12 h / |Sealed tube; |Reflux View Scheme

n-butyllithium 1.) THF, hexane, -50 deg C, 1.5 h, 2.) Et2O, from -50 deg C to RT; Yield given. Multistep reaction;