1: 92 percent / aq. Na2CO3 / Pd(Ph3P)4 / toluene; methanol / 12 h / Heating 2: 80 percent / aq. H2SO4; aq. NaNO2 / 0 °C 3: 33 percent / POBr3 / methoxybenzene / 3 h / Heating View Scheme

1: 92 percent / aq. Na2CO3 / Pd(Ph3P)4 / toluene; methanol / 12 h / Heating 2: 80 percent / aq. H2SO4; aq. NaNO2 / 0 °C 3: 33 percent / POBr3 / methoxybenzene / 3 h / Heating View Scheme

phosphorus oxytribromide in methoxybenzene 3 h; Heating;

1.1: 75 percent / periodic acid dihydrate; iodine; sulfuric acid / acetic acid; H2O / 4 h / 80 °C 2.1: 77 percent / hydrobromic acid; sodium nitrite; bromine / H2O / -5 - 20 °C 3.1: nBuLi; triisopropylborate / diethyl ether / -78 - 20 °C 3.2: 10 percent / acetic acid / diethyl ether 4.1: 57 percent / Pd(PPh3)4; aq. K3PO4 / dimethylformamide / 65 °C View Scheme

1.1: 77 percent / hydrobromic acid; sodium nitrite; bromine / H2O / -5 - 20 °C 2.1: nBuLi; triisopropylborate / diethyl ether / -78 - 20 °C 2.2: 10 percent / acetic acid / diethyl ether 3.1: 57 percent / Pd(PPh3)4; aq. K3PO4 / dimethylformamide / 65 °C View Scheme

1.1: nBuLi; triisopropylborate / diethyl ether / -78 - 20 °C 1.2: 78 percent / acetic acid / diethyl ether 2.1: 57 percent / Pd(PPh3)4; aq. K3PO4 / dimethylformamide / 65 °C View Scheme

1.1: nBuLi; triisopropylborate / diethyl ether / -78 - 20 °C 1.2: 10 percent / acetic acid / diethyl ether 2.1: 57 percent / Pd(PPh3)4; aq. K3PO4 / dimethylformamide / 65 °C View Scheme

Yield given. Multistep reaction. Yields of byproduct given;

1: 2-bromo-5-phenyl-pyridine With n-butyllithium in diethyl ether; hexane T=-60°C; 2 h; 2: N,N-dimethyl acetamide in diethyl ether; hexane 2 h; 3: With hydrogenchloride; water in diethyl ether; hexane T=20°C;