potassium hydroxide in ethanol 3.5 h; Heating;

1: 1-bromo-2-methoxymethoxy-3-methylsulfanylbenzene With tert.-butyl lithium in tetrahydrofuran; pentane T=-78°C; 1.5 h; 2: carbon dioxide in tetrahydrofuran; pentane T=-78°C; 1.5 h; 3: With hydrogenchloride in tetrahydrofuran; pentane T=20°C;

1: KHCO3 / dimethylformamide / Ambient temperature 2: 85 percent / KF, alumina / acetonitrile / 12 h / Ambient temperature 3: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 1 h, 2.) a) from -78 deg C to RT, b) RT, 24 h 4: 61 percent / aq. HCl / tetrahydrofuran / 6 h / 60 °C 5: 82 percent / aq. KOH / ethanol / 3.5 h / Heating View Scheme

1: 85 percent / KF, alumina / acetonitrile / 12 h / Ambient temperature 2: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 1 h, 2.) a) from -78 deg C to RT, b) RT, 24 h 3: 61 percent / aq. HCl / tetrahydrofuran / 6 h / 60 °C 4: 82 percent / aq. KOH / ethanol / 3.5 h / Heating View Scheme

1: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 1 h, 2.) a) from -78 deg C to RT, b) RT, 24 h 2: 61 percent / aq. HCl / tetrahydrofuran / 6 h / 60 °C 3: 82 percent / aq. KOH / ethanol / 3.5 h / Heating View Scheme

1: 61 percent / aq. HCl / tetrahydrofuran / 6 h / 60 °C 2: 82 percent / aq. KOH / ethanol / 3.5 h / Heating View Scheme

1.1: 99 percent / NaH / tetrahydrofuran; methyl acetate / 2 h / 0 - 20 °C 2.1: 78 percent / t-BuLi / diethyl ether; pentane / 1 h / -78 - 20 °C 3.1: t-BuLi / tetrahydrofuran; pentane / 1.5 h / -78 °C 3.2: tetrahydrofuran; pentane / 1.5 h / -78 °C 3.3: 67 percent / 6M HCl / tetrahydrofuran; pentane / 20 °C View Scheme

1.1: 78 percent / t-BuLi / diethyl ether; pentane / 1 h / -78 - 20 °C 2.1: t-BuLi / tetrahydrofuran; pentane / 1.5 h / -78 °C 2.2: tetrahydrofuran; pentane / 1.5 h / -78 °C 2.3: 67 percent / 6M HCl / tetrahydrofuran; pentane / 20 °C View Scheme