1: 1.3N HCl / 16 h / Ambient temperature 2: 1.) 30percent HBr, 2.) Ac2O / 1.) acetic acid, 50 deg C, 5 h, 2.) 50 deg C, 20 h, 3.) MeOH, RT, 42 h, then 45 deg C, 6 h View Scheme

1: 1.3N HCl / 16 h / Ambient temperature 2: 1.) 30percent HBr / 1.) acetic acid, 50 deg C, 6 h, 2.) acetic acid, 50 deg C, 19 h 3: H2 / 5percent Pd/C / dioxane; H2O / 1.25 h / 1520 Torr / Ambient temperature View Scheme

hydrogen bromide; hydrogen; acetic anhydride; palladium on activated charcoal 1.) acetic acid, 50 deg C, 21.5 h, 2.) 50 deg C, 5.5 h, 3.) dioxane, water, 2 atm, 30 min; Yield given. Multistep reaction. Yields of byproduct given;

1: 1.3N HCl / 16 h / Ambient temperature 2: 1.) 30percent HBr / 1.) acetic acid, 50 deg C, 6 h, 2.) acetic acid, 50 deg C, 19 h 3: H2 / 5percent Pd/C / dioxane; H2O / 1.25 h / 1520 Torr / Ambient temperature View Scheme

hydrogen bromide; hydrogen; acetic anhydride; palladium on activated charcoal 1.) acetic acid, 50 deg C, 21.5 h, 2.) 50 deg C, 5.5 h, 3.) dioxane, water, 2 atm, 30 min; Yield given. Multistep reaction. Yields of byproduct given;