lithium aluminium tetrahydride in tetrahydrofuran T=0°C; 1 h;

sodium tetrahydroborate in tetrahydrofuran; methanol T=25°C; 12 h;

1: NBS, AIBN / CCl4 / 0.25 h / Heating 2: ethanol / 1 h / Heating 3: 85percent aq. KOH / ethanol / Ambient temperature View Scheme

1: ethanol / 1 h / Heating 2: 85percent aq. KOH / ethanol / Ambient temperature View Scheme

1: 1.) n-BuLi / 1.) THF, -78 deg C, 5 min, 2.) THF, -78 deg C, 5 min 2: 93 percent / n-Bu4NI / dimethylformamide / 24 h / 80 °C 3: 100 percent / Dibal-H / toluene / 2 h / -78 deg C -> 0 deg C 4: 95 percent / HCl(g) 5: 1.) Wang resin, Huenig's base, 2.) 3percent Pd(PPh3)4, 2M Na2CO3, 3.) Br2, pyridine / 1.) DMF, 40-50 deg C, 2.) DME, reflux, 3.) DMF, 80-90 deg C, 24 h View Scheme

1: 93 percent / n-Bu4NI / dimethylformamide / 24 h / 80 °C 2: 100 percent / Dibal-H / toluene / 2 h / -78 deg C -> 0 deg C 3: 95 percent / HCl(g) 4: 1.) Wang resin, Huenig's base, 2.) 3percent Pd(PPh3)4, 2M Na2CO3, 3.) Br2, pyridine / 1.) DMF, 40-50 deg C, 2.) DME, reflux, 3.) DMF, 80-90 deg C, 24 h View Scheme

1: 100 percent / Dibal-H / toluene / 2 h / -78 deg C -> 0 deg C 2: 95 percent / HCl(g) 3: 1.) Wang resin, Huenig's base, 2.) 3percent Pd(PPh3)4, 2M Na2CO3, 3.) Br2, pyridine / 1.) DMF, 40-50 deg C, 2.) DME, reflux, 3.) DMF, 80-90 deg C, 24 h View Scheme

1.1: BuLi / hexane; tetrahydrofuran / 0.25 h / -100 °C 1.2: 91 percent / hexane; tetrahydrofuran / 25 °C 2.1: 96 percent / NaBH4 / methanol; tetrahydrofuran / 12 h / 25 °C View Scheme

1: 95 percent / HCl(g) 2: 1.) Wang resin, Huenig's base, 2.) 3percent Pd(PPh3)4, 2M Na2CO3, 3.) Br2, pyridine / 1.) DMF, 40-50 deg C, 2.) DME, reflux, 3.) DMF, 80-90 deg C, 24 h View Scheme

pyridine; tetrakis(triphenylphosphine) palladium(0); bromine; sodium carbonate; N-ethyl-N,N-diisopropylamine; Wang resin 1.) DMF, 40-50 deg C, 2.) DME, reflux, 3.) DMF, 80-90 deg C, 24 h; Yield given. Multistep reaction. Yields of byproduct given;