tetrakis(triphenylphosphine) palladium(0); triethylamine in N,N-dimethyl-formamide T=90°C; Carbomethoxylation; P=2068.65 Torr; 16 h;

sodium periodate; osmium(VIII) oxide in tetrahydrofuran; water; tert-butyl alcohol T=20°C; 2 h;

1: 2-fluoro-5-iodo-benzoic acid methyl ester With isopropylmagnesium chloride lithium chloride complex in tetrahydrofuran T=-45 - -40°C; 1 h; 2: N,N-dimethyl-formamide in tetrahydrofuran T=-40 - 20°C; 1 h; Product distribution / selectivity;

1: With N-bromosuccinmide in tetrachloromethane 20 h; Irradiation; 2: With water; silver nitrate in acetone

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide; acetonitrile / 20 °C 2: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 2 h / Reflux 3: osmium(VIII) oxide; sodium periodate / water; tert-butyl alcohol; tetrahydrofuran / 20 °C View Scheme

1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 2 h / Reflux 2: osmium(VIII) oxide; sodium periodate / water; tert-butyl alcohol; tetrahydrofuran / 20 °C View Scheme

1.1: 94 percent / K2CO3 / acetone / Heating 2.1: NBS / CCl4 / 20 h / Irradiation 2.2: 57 percent / AgNO3; H2O / acetone View Scheme