hydrogenchloride in 1,4-dioxane; water T=80°C; 4 h;

hydrogen; palladium on activated charcoal in methanol; ethyl acetate

1: 86 percent / AlBr3 / acetonitrile / 0.33 h / 0 - 5 °C 2: 89 percent / K2CO3 / acetone / Heating 3: 89 percent / AlBr3 / acetonitrile / 1 h / Ambient temperature 4: 95 percent / K2CO3 / methanol / 2 h / Heating 5: 89 percent / H2 / 10percent palladium on charcoal / ethyl acetate; methanol View Scheme

1: 89 percent / K2CO3 / acetone / Heating 2: 89 percent / AlBr3 / acetonitrile / 1 h / Ambient temperature 3: 95 percent / K2CO3 / methanol / 2 h / Heating 4: 89 percent / H2 / 10percent palladium on charcoal / ethyl acetate; methanol View Scheme

1: 1.) potassium benzoate, 2.) K2CO3 / 1.) 170/180 deg C, 8 h, 2.) acetone, reflux, 2.5-4 h 2: 86 percent / AlBr3 / acetonitrile / 0.33 h / 0 - 5 °C 3: 89 percent / K2CO3 / acetone / Heating 4: 89 percent / AlBr3 / acetonitrile / 1 h / Ambient temperature 5: 95 percent / K2CO3 / methanol / 2 h / Heating 6: 89 percent / H2 / 10percent palladium on charcoal / ethyl acetate; methanol View Scheme

1: 1.) potassium benzoate, 2.) K2CO3 / 1.) 170/180 deg C, 8 h, 2.) acetone, reflux, 2.5-4 h 2: 86 percent / AlBr3 / acetonitrile / 0.33 h / 0 - 5 °C 3: 89 percent / K2CO3 / acetone / Heating 4: 89 percent / AlBr3 / acetonitrile / 1 h / Ambient temperature 5: 95 percent / K2CO3 / methanol / 2 h / Heating 6: 89 percent / H2 / 10percent palladium on charcoal / ethyl acetate; methanol View Scheme

1: 95 percent / K2CO3 / methanol / 2 h / Heating 2: 89 percent / H2 / 10percent palladium on charcoal / ethyl acetate; methanol View Scheme

1: 89 percent / AlBr3 / acetonitrile / 1 h / Ambient temperature 2: 95 percent / K2CO3 / methanol / 2 h / Heating 3: 89 percent / H2 / 10percent palladium on charcoal / ethyl acetate; methanol View Scheme