1: Br2, Al 2: Cl2 / Irradiation View Scheme

1: 64 percent / n-butyl lithium / diethyl ether / -78 °C 2: 50 percent / aq. KOH / toluene / 20 °C View Scheme

1: 2,4-difluoro-1-bromobenzene With lithium diisopropyl amide in tetrahydrofuran T=-78°C; 1 h; 2: triethylsilyl chloride in tetrahydrofuran T=-78 - 0°C; 3: With water; ammonium chloride in tetrahydrofuran T=0°C;

1: With magnesium in tetrahydrofuran T=20°C; 3 h; Inert atmosphere; 2: With synthetic air; cobalt(II) chloride in tetrahydrofuran T=0°C; 3 h; Inert atmosphere;

potassium tert-butylate in 1,4-dioxane T=20°C; Inert atmosphere; regioselective reaction;

1.1: tetrahydrofuran / 5 h / 65 - 68 °C 2.1: AlCl3, aluminium chloride / 1,2-dichloro-ethane / 1 h / -10 - 5 °C 3.1: tetrahydrofuran / 1 h / -15 - 0 °C 4.1: trifluoroacetic acid; 1,1,3,3-tetramethyldisiloxane / 1,2-dichloro-ethane / 0.25 h / -20 - -10 °C 5.1: n-butyllithium / toluene; hexane; tetrahydrofuran / -80 - -35 °C / Inert atmosphere 5.2: 1 h / 15 - 20 °C / pH 2 View Scheme

1.1: tetrahydrofuran / 4 h / 65 °C 2.1: AlCl3, aluminium chloride / 1,2-dichloro-ethane / 1.17 h / 0 - 10 °C / Inert atmosphere; Large scale reaction 2.2: 0 - 20 °C / Large scale reaction 3.1: tetrahydrofuran / 3.5 h / -10 - 4 °C / Inert atmosphere; Large scale reaction 3.2: -10 - 20 °C / Large scale reaction 4.1: 1,1,3,3-tetramethyldisiloxane; trifluoroacetic acid / 1,2-dichloro-ethane / -20 - -5 °C / Inert atmosphere; Large scale reaction 5.1: potassium phosphate; [Ru(II)(η6-benzene)(μ-Cl)Cl]2; potassium acetate; triphenylphosphine / 1-methyl-pyrrolidin-2-one / 9 h / 110 - 130 °C / Inert atmosphere; Large scale reaction 6.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.75 h / 20 - 62 °C / Inert atmosphere; Large scale reaction 7.1: sodium tetrahydroborate / tetrahydrofuran; water / 17.92 h / 0 - 22 °C / Inert atmosphere; Large scale reaction 7.2: 0 - 20 °C / Inert atmosphere; Large scale reaction View Scheme

1.1: tetrahydrofuran / 4 h / 65 °C 2.1: AlCl3, aluminium chloride / 1,2-dichloro-ethane / 1.17 h / 0 - 10 °C / Inert atmosphere; Large scale reaction 2.2: 0 - 20 °C / Large scale reaction View Scheme

1: (Ph)2PCl2, Et3N / dimethylformamide / 6 h / 85 °C 2: H2 / 10percent Pd/C / ethyl acetate / 3102.9 Torr 3: 6N aq. H2CrO4 / acetone / 20 °C 4: oxalyl chloride, DMF / CH2Cl2 / 20 °C 5: AlCl3 / CS2 / 40 °C 6: NaBH4 / methanol / 0 °C 7: p-TsOH / benzene / 80 °C View Scheme

1.1: tetrahydrofuran / 4 h / 65 °C 2.1: AlCl3, aluminium chloride / 1,2-dichloro-ethane / 1.17 h / 0 - 10 °C / Inert atmosphere; Large scale reaction 2.2: 0 - 20 °C / Large scale reaction 3.1: tetrahydrofuran / 3.5 h / -10 - 4 °C / Inert atmosphere; Large scale reaction 3.2: -10 - 20 °C / Large scale reaction 4.1: 1,1,3,3-tetramethyldisiloxane; trifluoroacetic acid / 1,2-dichloro-ethane / -20 - -5 °C / Inert atmosphere; Large scale reaction View Scheme