hydrogenchloride in water T=130 - 140°C; Microwave irradiationSealed tube;

chloro-trimethyl-silane; sodium bromide in 1-methyl-pyrrolidin-2-one T=0 - 75°C; 16 h; TimeReagent/catalystConcentrationTemperatureSolventPressure;

1: With Mg(O-t-Bu)2 in 1-methyl-pyrrolidin-2-one; toluene T=25 - 75°C; 6 h; 2: With water; acetic acid in 1-methyl-pyrrolidin-2-one; water; acetic acid; toluene 1 h; 3: With hydrogen bromide in 1-methyl-pyrrolidin-2-one; water; toluene T=90 - 95°C;

1: LiOt-Bu / dimethylformamide; tetrahydrofuran / 1 h / 30 - 35 °C 2: 1.) bromotrimethylsilane, 2.) NaOH / 1.) acetonitrile, reflux, 2.) H2O, pH 3 View Scheme

1: 86 percent / conc. HCl / Ambient temperature 2: 91 percent / NH3 / 65 °C 3: 44 percent / NaH / dimethylformamide / 0 - 20 °C 4: 1.) TMSBr, 2.) H2O / 1.) MeCN, RT, 2.) acetone, 4 deg C View Scheme

1: 91 percent / NH3 / 65 °C 2: 44 percent / NaH / dimethylformamide / 0 - 20 °C 3: 1.) TMSBr, 2.) H2O / 1.) MeCN, RT, 2.) acetone, 4 deg C View Scheme

1: NaOH / dimethylformamide / 20 h / 140 °C 2: LiOt-Bu / dimethylformamide; tetrahydrofuran / 1 h / 30 - 35 °C 3: 1.) bromotrimethylsilane, 2.) NaOH / 1.) acetonitrile, reflux, 2.) H2O, pH 3 View Scheme

1: With chloro-trimethyl-silane; sodium iodide in 1-methyl-pyrrolidin-2-one T=23°C; 6 h; 2: With water in acetonitrile

1: 85 percent / sulfuric acid / Ambient temperature 2: 1.) chlorotrimethylsilane / 1) pyridine, room temperature, 1 h; 2) pyridine, room temperature, 2 h 3: sodium hydride / dimethylformamide / 48 h / Ambient temperature 4: sodium methoxide / dimethylformamide / Ambient temperature 5: 47 percent / bromotrimethylsilane / acetonitrile / Ambient temperature View Scheme

1: sodium hydride / dimethylformamide / 48 h / Ambient temperature 2: sodium methoxide / dimethylformamide / Ambient temperature 3: 47 percent / bromotrimethylsilane / acetonitrile / Ambient temperature View Scheme