1: 1-bromo-4-methoxy-2,5-bismethoxymethoxybenzene With methyllithium in tetrahydrofuran; diethyl ether T=-78 - -20°C; 1 h; 2: methyl iodide in tetrahydrofuran; diethyl ether T=-78°C; 1 h;

1.1: NaH / tetrahydrofuran / 0.17 h / 0 °C 1.2: 75 percent / tetrahydrofuran / 24 h 2.1: 89 percent / NaHCO3; pyridium hydrobromide perbromide / methanol / 0.42 h / 20 °C 3.1: MeLi / tetrahydrofuran; diethyl ether / 1 h / -78 - -20 °C 3.2: 90 percent / tetrahydrofuran; diethyl ether / 1 h / -78 °C View Scheme

1.1: 89 percent / NaHCO3; pyridium hydrobromide perbromide / methanol / 0.42 h / 20 °C 2.1: MeLi / tetrahydrofuran; diethyl ether / 1 h / -78 - -20 °C 2.2: 90 percent / tetrahydrofuran; diethyl ether / 1 h / -78 °C View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / -78 - 25 °C 1.2: 66 percent / tetrahydrofuran; hexane / 0.5 h / 0 °C 2.1: 95 percent / aqueous HCl / dioxane / 8 h / 50 °C View Scheme