1.1: sec-BuLi / tetrahydrofuran; cyclohexane / 2 h / -75 °C 1.2: 82 percent / 1,1,2-trichloro-1,2,2-trifluoroethane / tetrahydrofuran; cyclohexane / 1 h / -75 °C 2.1: BuLi / CH2Cl2; hexane / 6 h / -75 °C 2.2: CH2Cl2; hexane 2.3: 61 percent / aq. HCl / pH 1 3.1: 94 percent / ammonium formate / Pd/C / methanol / 20 h / 25 °C View Scheme

1: 1,3-difluoro-4-(methoxymethoxy)benzene With n-butyllithium in tetrahydrofuran; hexanes T=-70°C; Inert atmosphere; 2: carbon dioxide in tetrahydrofuran; hexanes T=-70°C;

1.1: sec.-butyllithium / tetrahydrofuran; hexane / 2 h / -78 °C 1.2: 1 h / -40 °C 2.1: water; sodium hydroxide / ethanol / 1 h / Reflux View Scheme

1.1: sec.-butyllithium / tetrahydrofuran; hexane / 2 h / -78 °C 1.2: 1 h / -40 °C 2.1: water; sodium hydroxide / ethanol / 1 h / Reflux 3.1: dichloromethane / 2 h / 20 °C 4.1: ammonium hydroxide / dichloromethane / 3 h / 0 - 20 °C 5.1: hydrogenchloride; water / methanol / 2 h / 20 °C View Scheme