1: H2 / 10percent Pd/C / ethyl acetate; acetic acid / 1 h / 2327.2 Torr 2: 1.) 10percent H2SO4, NaNO2, 2.) Cu-bronze / 1.) acetic acid, water, 20 min, 2.) acetic acid, water 3: 73 percent / boron tribromide / CH2Cl2 / 3 h / -78 °C View Scheme

Multi-step reaction with 2 steps 1: H2 / 10percent Pd/C / ethyl acetate; acetic acid / 1 h / 2327.2 Torr2: 1.) 10percent H2SO4, NaNO2, 2.) Cu-bronze / 1.) acetic acid, water, 20 min, 2.) acetic acid, water  

With  hydrogen; palladium on activated charcoal in  acetic acid; ethyl acetate P=2327.2 Torr; 1 h;