N-bromosuccinmide; diisopropylamine in dichloromethane T=20°C; Inert atmosphere;

copper; zinc in sodium hydroxide T=20°C; Dehalogenation; 2 h;

2-(n-morpholino)ethanesulfonic acid; VBrPO(AnI) bromoperoxidase; dihydrogen peroxide; sodium bromide in water; tert-butyl alcohol T=23°C; pH=6.2; Overall yield = 39 percent;

Amberlyst-A26 tribromide in dichloromethane 24 h; Ambient temperature; Title compound not separated from byproducts;

1: With toluene-4-sulfonic acid in water; acetonitrile T=20°C; 0.0833333 h; 2: With N-chloro-succinimide in water; acetonitrile T=20°C; 2 h; regioselective reaction;

N-bromosuccinmide; diisopropylamine in dichloromethane 1 h; Ambient temperature;

sulfuric acid Heating;

1: potassium carbonate / acetonitrile / 2 h / |Reflux; |Sealed tube 2: N-chloro-succinimide; palladium diacetate; trifluorormethanesulfonic acid / 1,2-dichloro-ethane / 14 h / 20 °C / |Sealed tube 3: hydrazine hydrate / 12 h / 20 °C / |Sealed tube View Scheme

1: hydrogenchloride; sulfuric acid; dihydrogen peroxide; N-hexadecyl-N,N,N-trimethylammonium bromide; sodium lauryl sulfate / water / 4 h / Micellar solution 2: sulfuric acid; dihydrogen peroxide; N-hexadecyl-N,N,N-trimethylammonium bromide; sodium lauryl sulfate; sodium bromide / 2 h / Micellar solution View Scheme

1: potassium carbonate / acetonitrile / 4 h / |Reflux; |Sealed tube 2: N-chloro-succinimide; palladium diacetate; sodium pyrosulphate; trifluorormethanesulfonic acid / 1,2-dichloro-ethane / 0.17 h / 20 °C / |Sealed tube 3: palladium diacetate; trifluorormethanesulfonic acid; N-bromosuccinmide / 1,2-dichloro-ethane / 6 h / 20 °C / |Sealed tube 4: hydrazine hydrate / 12 h / 20 °C / |Sealed tube View Scheme