1: 4-iodobenzoic acid ethyl ester With isopropylmagnesium chloride in tetrahydrofuran T=-20°C; 0.5 h; 2: 1-bromo-4-nitro-benzene in tetrahydrofuran T=-20°C; 2 h; 3: With sodium tetrahydroborate; iron(II) chloride in tetrahydrofuran; ethanol T=20°C; 2 h; Further stages.;

1.1: 139 mg / aq. HCl / diethyl ether / 20 °C 2.1: HBF4; NaNO2 / H2O / cooling 2.2: 71 percent / CH2Cl2 / 20 °C View Scheme

1.1: 139 mg / aq. HCl / diethyl ether / 20 °C 2.1: HBF4; NaNO2 / H2O / cooling 2.2: 71 percent / CH2Cl2 / 20 °C View Scheme

1.1: HBF4; NaNO2 / H2O / cooling 1.2: 71 percent / CH2Cl2 / 20 °C View Scheme

1.1: NaNO2; HBF4 / H2O / 1.5 h / 0 - 20 °C 1.2: 80 percent / CH2Cl2 / 25 °C 2.1: i-PrMgCl / tetrahydrofuran / 0.5 h / -20 °C 2.2: tetrahydrofuran / 1 h / -20 °C 2.3: tetrahydrofuran; 1-methyl-pyrrolidin-2-one / 2 h / 20 °C 3.1: 265 mg / Zn; AcOH; CF3CO2H / 2 h / 75 °C View Scheme

Multistep reaction;