1: SOCl2 / diethyl ether / 4 h / Heating 2: 1.80 g / AlCl3 / 1,2-dichloro-ethane / 18 h / Heating 3: NaBH4 / methanol; CH2Cl2 / 3 h / 20 °C 4: 0.30 g / aq. HCl / methanol; CH2Cl2 / 0.5 h / 20 °C View Scheme

sodium hydroxide

1: thien-3-yl bromide With n-butyllithium in diethyl ether; hexane T=-70°C; 0.25 h; 2: With sulfur in diethyl ether; hexane T=-70°C; 0.5 h; 3: bromoacetic acid,potassium salt in diethyl ether; hexane T=55°C; 1 h;

n-butyllithium; potassium carbonate; sulfur Yield given. Multistep reaction;

hydrogenchloride

1.1: SOCl2 / diethyl ether / 4 h / Heating 2.1: 1.80 g / AlCl3 / 1,2-dichloro-ethane / 18 h / Heating 3.1: NaBH4 / methanol; CH2Cl2 / 3 h / 20 °C 4.1: 0.30 g / aq. HCl / methanol; CH2Cl2 / 0.5 h / 20 °C 5.1: n-BuLi / hexane; diethyl ether / 0.25 h / -15 °C 5.2: 50 percent / hexane; diethyl ether / 20 °C View Scheme