bromine; triphenylphosphine 1.) MeCN, 0-10 deg C, rt, 1 h; 2.) MeCN, rt, 30 min; 3.) 120 deg C, 15 min;

N-bromosuccinmide; meta-chloroperoxybenzoic acid in tetrachloromethane Heating;

hydrogen bromide in chlorobenzene

1: 71 percent / LiAlH4 / diethyl ether / 2 h / Heating 2: 60 percent / 1.) Br2, Ph3P / 1.) MeCN, 0-10 deg C, rt, 1 h; 2.) MeCN, rt, 30 min; 3.) 120 deg C, 15 min View Scheme

1: sodium tetrahydroborate; methanol / 1 h / 0 - 20 °C 2: phosphorus tribromide / diethyl ether / 3 h / 0 - 20 °C View Scheme

1,3,5,7-tetra-azatricyclo[5.1.1.13,5]decane in acetic acid 4 h; Heating;

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;