palladium 10 on activated carbon; hydrogen in methanol 2 h;

1: boron tribromide / dichloromethane / 4 - 20 °C / Inert atmosphere 2: palladium 10 on activated carbon; hydrogen / methanol / 2 h View Scheme

1: Amberlyst 15E / toluene / 5 h / Reflux; Inert atmosphere 2: hydrogen / methanol; dichloromethane / 10 h / 60 °C / 22801.5 Torr / Inert atmosphere; Autoclave 3: dimethylsulfide borane complex / tetrahydrofuran / 4 - 20 °C / Inert atmosphere 4: boron tribromide / dichloromethane / 4 - 20 °C / Inert atmosphere 5: palladium 10 on activated carbon; hydrogen / methanol / 2 h View Scheme

1: hydrogen / methanol; dichloromethane / 10 h / 60 °C / 22801.5 Torr / Inert atmosphere; Autoclave 2: dimethylsulfide borane complex / tetrahydrofuran / 4 - 20 °C / Inert atmosphere 3: boron tribromide / dichloromethane / 4 - 20 °C / Inert atmosphere 4: palladium 10 on activated carbon; hydrogen / methanol / 2 h View Scheme

1: dimethylsulfide borane complex / tetrahydrofuran / 4 - 20 °C / Inert atmosphere 2: boron tribromide / dichloromethane / 4 - 20 °C / Inert atmosphere 3: palladium 10 on activated carbon; hydrogen / methanol / 2 h View Scheme

ammonium hydroxide; hydrogen bromide 3 h; Heating;

2: 30 percent / 1.) 48percent HBr aq., 2.) NH4OH / 3 h / Heating View Scheme