1: 1-(chloromethyl)-2-fluorobenzene With iodine; magnesium in diethyl ether 2 h; Heating / reflux; 2: cyclopropionyl chloride in tetrahydrofuran; diethyl ether T=-70 - 20°C; 3: With water; ammonium chloride Product distribution / selectivity;

1.1: tetrabutylammomium bromide / dichloromethane; water / 25 °C 2.1: sodium hydroxide; water / 5 - 95 °C 2.2: pH 2 - 3 3.1: magnesium; isopropyl bromide / toluene; tetrahydrofuran / 15 - 65 °C 3.2: 5 - 65 °C View Scheme

1.1: sodium hydroxide; water / 5 - 95 °C 1.2: pH 2 - 3 2.1: magnesium; isopropyl bromide / toluene; tetrahydrofuran / 15 - 65 °C 2.2: 5 - 65 °C View Scheme

1.1: triethylamine / dichloromethane / 0.25 h / 0 - 5 °C 1.2: 6 h / 0 - 5 °C 2.1: iodine; magnesium / tetrahydrofuran / 25 - 50 °C 2.2: 40 - 50 °C 2.3: 0.25 h / 0 - 30 °C View Scheme

hydrogenchloride; dihydrogen peroxide in 1,4-dioxane; water T=20 - 80°C; 2 - 72 h; Product distribution / selectivity;

1: 2,2'-azo-bisisobutyronitrile; acetic acid / ethyl acetate; water 2: tetrabutylammomium bromide; sodium bromide; potassium hydrogencarbonate / ethyl acetate; N,N-dimethyl-formamide; water View Scheme

bromine in methanol T=25 - 30°C; 6 h; Concentration;

1.1: toluene-4-sulfonic acid; 2,2'-azo-bisisobutyronitrile; N-bromosuccinmide / chloroform / 4 h / Reflux 2.1: potassium carbonate / acetonitrile / 5 h / 25 - 35 °C 3.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C 3.2: 1 h / -78 °C 3.3: 1 h / -60 - 0 °C 4.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 3.33 h / 10 - 30 °C View Scheme

1.1: toluene-4-sulfonic acid; 2,2'-azo-bisisobutyronitrile; N-bromosuccinmide / chloroform / 4 h / Reflux 2.1: potassium carbonate / acetonitrile / 5 h / 25 - 35 °C 3.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C 3.2: 1 h / -78 °C 3.3: 1 h / -60 - 0 °C View Scheme