in toluene T=100°C; 24 h;

1: N-bromosuccinimide; benzoyl peroxide / CCl4 / 5 h / Heating 2: 36.0 g / benzene / 20 °C View Scheme

bromine 1.) CCl4, irradiation; 2.) benzene; Yield given. Multistep reaction;

1: 95 percent / Zn, HBr / ethanol 2: NEt3 / CH2Cl2; toluene 3: 96 percent / MeONa / toluene / Heating View Scheme

1: 95 percent / Zn, HBr / ethanol 2: NEt3 / CH2Cl2; toluene 3: 97 percent / MeONa / toluene / Heating View Scheme

in hexane; benzene T=40°C; 168 h; Title compound not separated from byproducts;

1,8-diazabicyclo[5.4.0]undec-7-ene in acetonitrile T=60°C; Product distribution; Further Variations:Reaction partnersReagents;

1.1: 85 percent / K2CO3; dibenzo-18-crown-6 / CH2Cl2 / 16 h / 20 °C 2.1: tetrahydrofuran / 1 h / 20 °C 3.1: 14 percent / HCl; H2O / tetrahydrofuran / 24 h / 20 °C 4.1: Et3N / CH2Cl2 / 1 h / 20 °C 5.1: 80 percent / nitrobenzene / 0.2 h / 150 °C / microwave irradiation 6.1: 82 percent / K2CO3 / dimethylformamide / 2 h / 60 °C 7.1: 91 percent / H2 / Pd/C / ethanol / 5 h / 20 °C 8.1: NaNO2; H2SO4 / H2O / 0.5 h / 0 °C 8.2: 85 percent / NaN3 / H2O / 5 h / 20 °C 9.1: nitrobenzene; toluene / 0.75 h / 20 °C 10.1: nitrobenzene; toluene / 0.5 h / 150 - 180 °C / microwave irradiation View Scheme

1.1: potassium carbonate / dimethyl sulfoxide / 2 h / 20 °C 1.2: 18 h / 20 °C 2.1: [Rh(CO)2(Me2NCH2CH2NMe2)][RhCl2(CO)2]; carbon monoxide / tetrahydrofuran / 20 h / 100 °C / 5171.62 Torr / Autoclave View Scheme

1: 1.) K2CO3, dibenzo-18-crown-6, 2.) PhSH, AIBN / 1.) CH2Cl2, r.t., 16 h, 2.) benzene, reflux, 5 h 2: 85 percent / Fe, AcOH / ethanol / 2 h / Heating 3: 1.) Br2, 2.) Et3N / 1.) C6H6, 0 deg C, 1 h, 2.) C6H6, reflux, 5 h 4: toluene / 0 - 20 °C 5: toluene / 14 h / Heating 6: 85 percent / CuI, NaH / bis-(2-methoxy-ethyl) ether / 1.) r.t., 30 min, 2.) r.t., 30 h 7: 90 percent / TBAF / tetrahydrofuran / 6 h / Heating View Scheme