1: 4-bromo-3,5-dimethylisoxazole With n-butyllithium in tetrahydrofuran T=-65°C; 0.5 h; 2: tri-isopropoxy-borane in tetrahydrofuran T=-78 - 20°C; 16 h; 3: With water; ammonium chloride T=20°C;

1.1: N-bromosuccinmide / N,N-dimethyl-formamide / 3 h / 75 °C 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -65 °C 2.2: 16 h / -78 - 20 °C 2.3: 20 °C View Scheme

(i) EtMgBr, Et2O, THF, (ii) B(OMe)3, (iii) aq. HCl; Multistep reaction;

sodium hydroxide; iodine

1.1: Ba(OH)2·8H2O / tetrakis(triphenylphosphine) palladium(0) / ethylene glycol dimethyl ether; water / 16 h / 80 °C 2.1: hydrogen; acetic acid / palladium 10 on activated carbon / ethanol / 24 h 3.1: 1 h / 130 °C 4.1: diphenylether / 0.75 h / 255 °C 5.1: sodium hydroxide; ethanol / Reflux 5.2: pH 4 6.1: trichlorophosphate / N,N-dimethyl-formamide / 5 h / Reflux 6.2: 1 h / 0 - 5 °C 7.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 120 °C 8.1: potassium hydroxide; [bis(acetoxy)iodo]benzene / methanol / Cooling with ice View Scheme

sodium carbonate; tetrakis(triphenylphosphine) palladium(0) in water; N,N-dimethyl-formamide T=160°C; 0.25 h; sealed tubemicrowave irradiation;