sodium hydroxide in N,N-dimethyl-formamide T=100°C; Alkylation; 16 h;

bromine in tetrachloromethane T=70°C;

1: 87 percent / NaOH / dimethylformamide / 120 °C 2: 85 percent / Br2 / CCl4 / 70 °C View Scheme

1: 87 percent / NaOH / dimethylformamide / 120 °C 2: 85 percent / Br2 / CCl4 / 70 °C View Scheme

1.1: 97 percent / HNO3 / CHCl3; acetic acid / 18 h / 20 °C 2.1: 92 percent / aq. HCl; tin / tetrahydrofuran / 18 h / 20 °C 3.1: BF3*Et2O; tBuNO2 / tetrahydrofuran / 3 h / -8 °C 3.2: 95 percent / K2CO3; H2O; acetonitrile / tetrahydrofuran / 0.25 h / -15 °C 4.1: 62 percent / Cu(OAc)2 / PdCl2; PPh3 / triethylamine / 18 h / 100 °C 5.1: 88 percent / MeI / 18 h / 120 °C View Scheme