1: With N-bromosuccinmide in DMF (N,N-dimethyl-formamide) T=0 - 20°C; 13.5 h; 2: With water in dichloromethane 0.166667 h;

tetrakis(triphenylphosphine) palladium(0); sodium carbonate in toluene Suzuki Coupling; RefluxInert atmosphere;

1: Br2 / acetic acid 2: aq. KOH, EtOH 3: aq. NaNO2, aq. H3PO2 View Scheme

1: aq. KOH, EtOH 2: aq. NaNO2, aq. H3PO2 View Scheme

n-butyllithium in diethyl ether; hexane T=-10 - 25°C;

1.1: 98 percent / boron tribromide / CH2Cl2 / 1 h / 0 °C 2.1: 58.1 percent / potassium carbonate; potassium iodide / dimethylformamide / 24 h / 150 °C 3.1: t-butyllithium / tetrahydrofuran / 1 h / -78 °C 3.2: 68 percent / tetrahydrofuran / -78 - 20 °C 4.1: 94 percent / hydrochloric acid / acetic acid / 22 h / 20 °C View Scheme

(i) Mg, (ii) /BRN= 471223/, (iii) polyphosphoric acid; Multistep reaction;

1: 96 percent / BuLi / diethyl ether; hexane / -10 - 25 °C 2: 74 percent / KHCO3 / dimethylformamide / 24 h / 25 °C View Scheme