B4NF*3H2O in tetrahydrofuran T=25°C; 0.5 h;

bromine in tetrachloromethane

bromine; hydrogen fluoride; titanium tetrachloride T=0 - 20°C; 2.33333 h;

1.1: secBuLi / tetrahydrofuran; cyclohexane / 2 h / -75 °C 1.2: 95 percent / Br2 / tetrahydrofuran; cyclohexane / -75 °C 2.1: 85 percent / (iPr)2NH; BuLi / tetrahydrofuran; hexane / 2 h / -75 °C 3.1: 79 percent / B4NF*3H2O / tetrahydrofuran / 0.5 h / 25 °C View Scheme

1: 85 percent / (iPr)2NH; BuLi / tetrahydrofuran; hexane / 2 h / -75 °C 2: 79 percent / B4NF*3H2O / tetrahydrofuran / 0.5 h / 25 °C View Scheme

1.1: sodium salt of phosphorous acid; tri-tert-butyl phosphine / bis(dibenzylideneacetone)-palladium(0) / toluene; hexanes / 0.83 h / 23 °C / Inert atmosphere 1.2: 70 °C 2.1: hydrogenchloride / water; dimethyl sulfoxide / 40 - 75 °C 3.1: tetra-n-octylammonium bromide; potassium hydroxide / water / 1 h / 70 °C 4.1: sodium hydroxide; water / ethanol / 80 °C View Scheme

1: 5-bromo-2,2-difluorobenzo[d][1,3]dioxole With n-butyllithium in tetrahydrofuran 0.166667 h; Cooling with acetone-dry ice; 2: N,N-dimethyl-formamide in tetrahydrofuran T=20°C; 2 h; Cooling with acetone-dry ice; 3: With water; ammonium chloride in tetrahydrofuran

1.1: triethylamine / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 24 h / 100 °C 2.1: sodium hydroxide / methanol / 20 °C 2.2: pH 3 View Scheme

3,4,5,6-tetramethyl-t-Bu-X-Phos; potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0) in 1,4-dioxane; water T=100°C;

1.1: bis(dibenzylideneacetone)-palladium(0); sodium salt of phosphorous acid; tri-tert-butyl phosphine / toluene; hexane / 0.85 h / 23 °C / |Inert atmosphere 1.2: 0.75 h / 70 °C / |Inert atmosphere 2.1: hydrogenchloride / dimethyl sulfoxide; water / 1.33 h / 40 - 75 °C 3.1: potassium hydroxide; tetra-n-octylammonium bromide / water / 1 h / 70 °C 4.1: sodium hydroxide; water / ethanol / 80 °C 5.1: thionyl chloride / toluene / 0.5 h / 60 °C 6.1: triethylamine; 4-(N,N-dimethlyamino)pyridine / toluene / 2 h 7.1: hydrogenchloride; water / acetonitrile / 40 - 45 °C View Scheme