bromine; sodium acetate in acetic acid

1: 77 percent / Sn, conc. HCl 2: 55 percent / Br2, NaOAc / acetic acid View Scheme

1: 93 percent / KOH, nBu4NBr / CH2Cl2; H2O 2: 77 percent / Sn, conc. HCl 3: 55 percent / Br2, NaOAc / acetic acid View Scheme

1: 1) NaNO2, conc. H2SO4, 2) 60percent H2SO4 2: 38 percent / conc. HNO3 / propionic acid / -10 °C 3: 93 percent / KOH, nBu4NBr / CH2Cl2; H2O 4: 77 percent / Sn, conc. HCl 5: 55 percent / Br2, NaOAc / acetic acid View Scheme