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.;

sodium methylate in dimethyl sulfoxide 2 h; Heating;

(CH3)4Br in liquid sulphur dioxide T=-23°C; Rate constantProduct distribution;

in methanol; dimethyl sulfoxide Reflux;

hydrogenchloride; sodium hypophosphite; sulfuric acid; sodium nitrite in acetic acid 1.) -5 deg C, 2 h, 2.) 0 deg C, 12 h;;

1.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 2 h / -78 °C / Inert atmosphere 1.2: 0.5 h / -78 °C / Inert atmosphere 2.1: methanol; dimethyl sulfoxide / Reflux View Scheme

1: 1.) aq. H2SO4, NaNO2, 2.) Cu2Br2, CuSO4, conc. HBr; / 1.) -5 deg C, 5 min, 2.) 0 deg C, 3.) 1-5 deg C, 1.5 h, 4.) 50 deg C, 30 min; 2: 58 percent / Fe fillings, conc. HCl / acetic acid / 6 h / 50 °C 3: 26 percent / aq. H2SO4, aq. HCl, NaNO2, aq. NaH2PO2; / acetic acid / 1.) -5 deg C, 2 h, 2.) 0 deg C, 12 h; View Scheme

1: 58 percent / Fe fillings, conc. HCl / acetic acid / 6 h / 50 °C 2: 26 percent / aq. H2SO4, aq. HCl, NaNO2, aq. NaH2PO2; / acetic acid / 1.) -5 deg C, 2 h, 2.) 0 deg C, 12 h; View Scheme

1: 83 percent / Br2 / acetic acid / 0.33 h / 20 °C 2: 1.) aq. H2SO4, NaNO2, 2.) Cu2Br2, CuSO4, conc. HBr; / 1.) -5 deg C, 5 min, 2.) 0 deg C, 3.) 1-5 deg C, 1.5 h, 4.) 50 deg C, 30 min; 3: 58 percent / Fe fillings, conc. HCl / acetic acid / 6 h / 50 °C 4: 26 percent / aq. H2SO4, aq. HCl, NaNO2, aq. NaH2PO2; / acetic acid / 1.) -5 deg C, 2 h, 2.) 0 deg C, 12 h; View Scheme

in pyridine; methanol T=115°C; Rate constantProduct distribution;