N-bromosuccinmide in N,N-dimethyl-formamide T=0 - 20°C; 2.5 h;

sodium acetate in acetic acid

1: N-bromosuccinmide / N,N-dimethyl-formamide / 2.5 h / 0 - 20 °C 2: sodium amide / ammonia / 2 h / 20 °C / |liquid NH3 View Scheme

1: With trifluoroacetic acid 6 h; Heating / reflux; 2: With ammonia in water; trifluoroacetic acid

potassium hydroxide in methanol

1: bromine; sodium acetate; acetic acid 2: ammonia; sodium; anhydrous iron chloride / 2 h / 20 °C 3: borane-THF / ethanol; tetrahydrofuran / 13 h View Scheme

1.1: bromine; sodium acetate; acetic acid 2.1: ammonia; sodium; anhydrous iron chloride / 2 h / 20 °C 3.1: borane-THF / ethanol; tetrahydrofuran / 13 h 4.1: triethylamine / dichloromethane / 20 °C 5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / |Reflux 6.1: ethanol 7.1: sodium hydroxide / ethyl acetate 7.2: 18 h / |Reflux 8.1: hydrogen; 10 palladium hydroxide on charcoal / acetic acid / 24 h / 20 °C / 3675.37 Torr View Scheme

lithium aluminium tetrahydride in tetrahydrofuran

pyridine; methanol; sodium tetrahydroborate T=100°C; 9 h;

tetrabutylammomium bromide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in acetonitrile T=20°C; 0.0833333 h; Inert atmosphereMolecular sieve;