1: With HNO2 2: With potassium iodide

1: With isopropylmagnesium chloride in tert-butyl methyl ether T=0°C; Grignard Reaction; 2: With hydrogenchloride; water

1: 5-bromo-2-iodo-1,3-dimethyl-benzene With n-butyllithium in tetrahydrofuran; hexane T=-75 - -70°C; 0.5 h; 2: boric acid trimethyl ester in tetrahydrofuran; hexane T=-75 - 20°C; 3 h;

1.1: n-BuLi / hexane; diethyl ether / 3 h / -78 °C 1.2: 67 percent / tetrahydrofuran; hexane; diethyl ether / 20 °C 2.1: 97 percent / HCl gas / methanol; benzene / 1 h 3.1: 76 percent / AgBF4; CH3Cl / CH2Cl2 / Heating 4.1: N2O4; NaOAc / CCl4 / -20 - 20 °C 5.1: 421 mg / t-BuOK / tetrahydrofuran 6.1: 20 percent / CuI; (PPh3)2PdCl2; Et3N / 35 °C 7.1: 98 percent / aq. NaOH; t-BuOH / 20 °C View Scheme