tetrabutylammomium bromide; tetra(n-butyl)ammonium hydroxide in water T=25 - 50°C; Hydrolysis; Kinetics;

2: LiAlH4 3: K2CO3 View Scheme

1: 70 percent / Br2, AcOH / 48 h / Ambient temperature 2: 87 percent / K2CO3 / dimethylformamide / 24 h / 60 °C 3: 1.) BuLi, CuBr*SMe2, 2.) Me3SiCl / 1.) Et2O, hexane, THF, -78 deg C, 1 h, 2.) THF, Et2O, hexane, -78 deg C, 1.5 h View Scheme

1: 70 percent / Br2, AcOH / 48 h / Ambient temperature 2: 87 percent / K2CO3 / dimethylformamide / 24 h / 60 °C View Scheme

in benzene 22 h; Ambient temperature; Yields of byproduct given;

1: 70 percent / Br2, AcOH / 48 h / Ambient temperature 2: 87 percent / K2CO3 / dimethylformamide / 24 h / 60 °C 3: 1.) BuLi, CuBr*SMe2, 2.) Me3SiCl / 1.) Et2O, hexane, THF, -78 deg C, 1 h, 2.) THF, Et2O, hexane, -78 deg C, 1.5 h 4: 92 percent / Et3N*HF / tetrahydrofuran / 120 h / Ambient temperature 5: 50 percent / Jones reagent / acetone / 3 h / 0 - 20 °C 6: 1.) N-methylmorpholine, isobutyl chloroformate, 2.) N-hydroxy-2-thiopyridone, Et3N / 1.) THF, -15 deg C, 15 min, 2.) Et2O, THF, -15 deg C, 1 h View Scheme

1: Br2; AcOH / 20 °C 2: K2CO3 / methanol / 20 °C 3: 88 percent / iPr2NEt / CH2Cl2 / 4 h / 0 - 20 °C View Scheme

tetrabutylammomium bromide; tetra(n-butyl)ammonium hydroxide in water T=25 - 50°C; Hydrolysis; Kinetics;