1: With sodium t-butanolate in tetrahydrofuran T=10 - 20°C; 1.5 h; 2: With hydrogenchloride in tetrahydrofuran; water T=0 - 5°C; 1.75 h;

1: (E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide With N-bromosuccinmide in tetrahydrofuran; water T=0 - 22°C; 3 h; 2: 1-(6-chloro-2-methylpyrimidin-4-yl)thiourea in tetrahydrofuran; water 2 h; Heating / reflux;

trifluorormethanesulfonic acid; trifluoroacetic acid in dichloromethane T=20°C; 3 h;

1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 - -75 °C 1.2: 86 percent / tetrahydrofuran; hexane / 2 h / -78 °C 2.1: NaH / dimethylformamide / 0.5 h 2.2: 95 percent / Bu4NI / dimethylformamide / 16 h / 20 °C 3.1: NaH / tetrahydrofuran / 0.5 h / 0 °C 3.2: 83 percent / tetrahydrofuran / 4 h / Heating 4.1: 99 percent / CF3CO2H; CF3SO3H / CH2Cl2 / 3 h / 20 °C View Scheme

1.1: NaH / dimethylformamide / 0.5 h 1.2: 95 percent / Bu4NI / dimethylformamide / 16 h / 20 °C 2.1: NaH / tetrahydrofuran / 0.5 h / 0 °C 2.2: 83 percent / tetrahydrofuran / 4 h / Heating 3.1: 99 percent / CF3CO2H; CF3SO3H / CH2Cl2 / 3 h / 20 °C View Scheme

1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C 1.2: 83 percent / tetrahydrofuran / 4 h / Heating 2.1: 99 percent / CF3CO2H; CF3SO3H / CH2Cl2 / 3 h / 20 °C View Scheme

1: i-Pr2NEt / tetrahydrofuran 2: TFA / CH2Cl2 3: NaH / tetrahydrofuran View Scheme

1: TFA / CH2Cl2 2: NaH / tetrahydrofuran View Scheme

1: NaNO2; CuBr 2: NaH View Scheme

sodium hydride