1: 4-chloro-1-{[(4-chloro-2-fluorophenyl)methyl]oxy}-2-iodobenzene With isopropylmagnesium chloride in tetrahydrofuran T=-10°C; 0.5 h; 2: 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in tetrahydrofuran T=-10 - 20°C; 18 h; Product distribution / selectivity;

1: 4-chloro-1-{[(4-chloro-2-fluorophenyl)methyl]oxy}-2-iodobenzene With isopropylmagnesium chloride in tetrahydrofuran; diethyl ether T=-12 - -9°C; 0.633333 h; 2: iPrB(pinacolate) in tetrahydrofuran; diethyl ether T=-10 - 20°C; Product distribution / selectivity;

1: 4-chloro-1-{[(4-chloro-2-fluorophenyl)methyl]oxy}-2-iodobenzene; isopropylmagnesium chloride in toluene T=-10 - -3°C; 2: 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in toluene T=0 - 20°C;

1: 4-chloro-1-{[(4-chloro-2-fluorophenyl)methyl]oxy}-2-iodobenzene With isopropylmagnesium chloride in tetrahydrofuran; toluene T=-12 - -5°C; Large scale reaction; 2: 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in tetrahydrofuran; toluene T=10 - 22°C; Large scale reaction;

1: 4-chloro-2-iodo phenol; 4-chloro-2-fluoro-benzyl bromide With potassium carbonate in acetone T=21°C; 1 h; RefluxLarge scale; 2: isopropylmagnesium chloride in tetrahydrofuran T=-12 - -5°C; Large scale; 3: 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane T=10 - 50°C; Large scale;

1.1: potassium carbonate / acetone / 1 h / Reflux; Large scale reaction 2.1: isopropylmagnesium chloride / tetrahydrofuran; toluene / -12 - -5 °C / Large scale reaction 2.2: 10 - 22 °C / Large scale reaction View Scheme

1.1: boron tribromide / dichloromethane 2.1: potassium carbonate / acetone / 1 h / Reflux; Large scale reaction 3.1: isopropylmagnesium chloride / tetrahydrofuran; toluene / -12 - -5 °C / Large scale reaction 3.2: 10 - 22 °C / Large scale reaction View Scheme