hydrogenchloride; acetic acid; tin(ll) chloride T=100°C; 1 h;

1: 3.99 g / BBr3 / CH2Cl2 / 0 - 20 °C 2: 62 percent / Br2; acetic acid / 1 h / 100 °C 3: 41 percent / SnCl2; aq. HCl; acetic acid / 1 h / 100 °C View Scheme

1.1: methanol / 1.5 h / Heating 2.1: K2CO3 / acetone / 6 h / Heating 3.1: aq. HCl / 5 h / Heating 4.1: aq. HCl; NaNO2 / 0.5 h / 10 °C 4.2: aq. HBF4 4.3: xylene / 1 h / Heating 5.1: 3.99 g / BBr3 / CH2Cl2 / 0 - 20 °C 6.1: 62 percent / Br2; acetic acid / 1 h / 100 °C 7.1: 41 percent / SnCl2; aq. HCl; acetic acid / 1 h / 100 °C View Scheme

1.1: aq. HCl / 5 h / Heating 2.1: aq. HCl; NaNO2 / 0.5 h / 10 °C 2.2: aq. HBF4 2.3: xylene / 1 h / Heating 3.1: 3.99 g / BBr3 / CH2Cl2 / 0 - 20 °C 4.1: 62 percent / Br2; acetic acid / 1 h / 100 °C 5.1: 41 percent / SnCl2; aq. HCl; acetic acid / 1 h / 100 °C View Scheme

1.1: aq. HCl; NaNO2 / 0.5 h / 10 °C 1.2: aq. HBF4 1.3: xylene / 1 h / Heating 2.1: 3.99 g / BBr3 / CH2Cl2 / 0 - 20 °C 3.1: 62 percent / Br2; acetic acid / 1 h / 100 °C 4.1: 41 percent / SnCl2; aq. HCl; acetic acid / 1 h / 100 °C View Scheme

1.1: K2CO3 / acetone / 6 h / Heating 2.1: aq. HCl / 5 h / Heating 3.1: aq. HCl; NaNO2 / 0.5 h / 10 °C 3.2: aq. HBF4 3.3: xylene / 1 h / Heating 4.1: 3.99 g / BBr3 / CH2Cl2 / 0 - 20 °C 5.1: 62 percent / Br2; acetic acid / 1 h / 100 °C 6.1: 41 percent / SnCl2; aq. HCl; acetic acid / 1 h / 100 °C View Scheme

1: 1.) sodium nitrite, conc. HCl, 2.) HBF4 / 1.) water, 0 deg C, 30 min, 2.) 0 deg C, 30 min 2: 66 percent / xylene / 1 h / Heating 3: 86 percent / aq. HBr / acetic acid / 4 h / Heating 4: 1.) bromine, 2.) SnCl2, conc. HCl / 1.) glacial acetic acid, heated on a steam bath, 1 h, then RT, overnight, 2.) glacial acetic acid, heated on a steam bath, 1 h View Scheme

hydrogenchloride; bromine; tin(ll) chloride 1.) glacial acetic acid, heated on a steam bath, 1 h, then RT, overnight, 2.) glacial acetic acid, heated on a steam bath, 1 h; Yield given. Multistep reaction;