1: 79 percent / NaHCO3; NaHCO2; tetrabutylammonium bromide / Pd-benzothiazole carbene complex / 8 h / 130 °C 2: 87 percent / NaOH / methanol; H2O / 20 h / 23 °C View Scheme

anhydrous iron chloride; N-bromosuccinmide in acetonitrile T=60°C; 5 h; Inert atmosphere;

pyridine T=20°C; 2.5 h; Inert atmosphere;

triethylamine in tetrahydrofuran

1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / Inert atmosphere 2: N-bromosuccinmide; anhydrous iron chloride / acetonitrile / 5 h / 60 °C / Inert atmosphere View Scheme

1: With lithium chloride; zinc in tetrahydrofuran T=50°C; 14 h; Inert atmosphere; 2: With water; ammonium chloride in tetrahydrofuran Inert atmosphere; regioselective reaction;

1: tert-butyl 2,4-dibromophenyl carbonate With lithium chloride; zinc in tetrahydrofuran T=50°C; 14 h; Inert atmosphere; 2: 3-iodo-α,α,α-trifluorotoluene With trifuran-2-yl-phosphane; bis(dibenzylideneacetone)-palladium(0) in tetrahydrofuran T=25°C; Negishi coupling reaction; 12 h; Inert atmosphere; regioselective reaction;

iron (III) acetylacetonate; 1,1-dimethylethylmagnesium chloride in tetrahydrofuran T=10°C; 1.5 h; Inert atmosphere;