hydrogen; palladium on activated charcoal in ethyl acetate 1 h;

N-bromosuccinmide; dibenzoyl peroxide in tetrachloromethane

1: 80 percent / H2 / 10percent Pd/C / ethyl acetate / 1 h 2: 67 percent / AlCl3 / CH2Cl2 / 0.25 h / Heating 3: 1.) NaNH2 / 1.) THF, 1 h, 2.) THF, 30 min View Scheme

1: 80 percent / H2 / 10percent Pd/C / ethyl acetate / 1 h 2: 67 percent / AlCl3 / CH2Cl2 / 0.25 h / Heating View Scheme

1: 80 percent / H2 / 10percent Pd/C / ethyl acetate / 1 h 2: 67 percent / AlCl3 / CH2Cl2 / 0.25 h / Heating 3: 1.) NaNH2 / 1.) THF, 1 h, 2.) THF, 30 min 4: 85 percent / aq. 5N KOH / methanol / 0.17 h / Heating View Scheme