n-butyllithium; boron triethoxide; N,N,N',N,-tetramethylethylenediamine in tetrahydrofuran; pentane T=-100°C; 0.0833333 h;

n-butyllithium in tetrahydrofuran; hexane T=-90 - -80°C; 0.25 h; Inert atmosphere;

1.1: KOH / ethanol / 1 h / 60 °C 1.2: aq. NaOCl / 1 h / 0 °C 2.1: PPh3 / xylene / 3 h / 140 °C 3.1: 45 percent / n-BuLi; TMEDA; B(OEt)3 / tetrahydrofuran; pentane / 0.08 h / -100 °C View Scheme

1.1: 93 percent / N-bromosuccinimide; AcOH / 2 h / 60 °C 2.1: KOH / ethanol / 1 h / 60 °C 2.2: aq. NaOCl / 1 h / 0 °C 3.1: PPh3 / xylene / 3 h / 140 °C 4.1: 45 percent / n-BuLi; TMEDA; B(OEt)3 / tetrahydrofuran; pentane / 0.08 h / -100 °C View Scheme

1: PPh3 / xylene / 3 h / 140 °C 2: 45 percent / n-BuLi; TMEDA; B(OEt)3 / tetrahydrofuran; pentane / 0.08 h / -100 °C View Scheme

sodium carbonate; tris-(o-tolyl)phosphine; bis(dibenzylideneacetone)-palladium(0) in N,N-dimethyl-formamide T=110°C; Suzuki coupling; 2 h;

1: Pd(dba)2; P(o-tol)3; 2 N aq. Na2CO3 / dimethylformamide; toluene / 3 h / 110 °C 2: 40 percent / NaNO2 / dimethylformamide / 3 h / 20 °C 3: 68 percent / Pd(dba)2; PPh3; 2 N aq. Na2CO3 / dimethylformamide / 2 h / 80 °C View Scheme