1: With tert.-butyl lithium in diethyl ether T=-70°C; Metallation; 2: With boric acid trimethyl ester in diethyl ether T=-70 - -20°C; Substitution; 3: With sulfuric acid; dihydrogen peroxide in diethyl ether; acetic acid T=-20 - 35°C; Substitution; 1 h;

1.1: H2 / 5 percent Pd/C / tetrahydrofuran 2.1: HBr; NaNO2 2.2: 46 percent / CuBr / 20 - 80 °C 3.1: t-BuLi / diethyl ether / -70 °C 3.2: B(OMe)3 / diethyl ether / -70 - -20 °C 3.3: 58 percent / H2O2; H2SO4 / acetic acid; diethyl ether / 1 h / -20 - 35 °C View Scheme

1.1: HBr; NaNO2 1.2: 46 percent / CuBr / 20 - 80 °C 2.1: t-BuLi / diethyl ether / -70 °C 2.2: B(OMe)3 / diethyl ether / -70 - -20 °C 2.3: 58 percent / H2O2; H2SO4 / acetic acid; diethyl ether / 1 h / -20 - 35 °C View Scheme

1: dichloromethane / 1 h / 0 °C 2: trifluoroacetic acid / 12 h / 70 °C View Scheme

1: dichloromethane / 1 h / 0 °C 2: trifluoroacetic acid / 24 h / 70 °C View Scheme

T=20°C; 312 h; TemperatureTime;