1: With hydrogen bromide; sodium nitrite in water T=-5°C; 0.166667 h; 2: With hydrogen bromide; copper(I) bromide in water T=20°C; Sandmeyer reaction; 4 h; Heating;

1: With 2,2,6,6-tetramethylpiperidinyl-lithium in tetrahydrofuran T=0°C; 2 h; 2: With dibromotetrachlorochloroethane in tetrahydrofuran T=0 - 65°C; 2.5 h; 3: With hydrogenchloride T=20°C;

1: 1,2-dibromo-3-methoxybenzene With isopropylmagnesium chloride in tetrahydrofuran T=-40°C; 2 h; 2: carbon dioxide With hydrogenchloride in tetrahydrofuran 1 h; Further stages.;

permanganate(VII) ion; sodium carbonate

1: 97 percent / H2, aq. NaHCO3 / Pd/C 2: 73 percent / diazotization View Scheme

1.1: 60 percent / MeONa / dimethylsulfoxide / 2 h / Heating 2.1: i-PrMgCl / tetrahydrofuran / 2 h / -40 °C 2.2: aq. HCl / tetrahydrofuran / 1 h View Scheme

1.1: n-BuLi; N,N',N'-trimethylenediamine / hexane; toluene / 0.25 h / 20 °C 1.2: phenyllithium / various solvents / 8 h / 20 °C 1.3: 96 percent / 1,2-dibromotetrafluoroethane / various solvents / -78 - 20 °C 2.1: KMnO4 / acetone; H2O / 55 °C View Scheme