lithium diisopropyl amide in tetrahydrofuran; hexane -78 deg C, 30 min; -78 to 5 deg C;

lithium; diisopropylamine in tetrahydrofuran; water

1: ortho-fluorobromobenzene With lithium diisopropyl amide in tetrahydrofuran; hexane T=-78°C; 0.833333 h; 2: carbon dioxide With sodium carbonate in tetrahydrofuran; hexane; water T=20°C;

sulfuric acid 8 h; Heating;

1: sulfuric acid / 1 h / |Reflux 2: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene; caesium carbonate / 90 °C / |Sealed tube; |Inert atmosphere 3: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 4: pyridine / dichloromethane / 20 °C 5: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 20 °C / |Cooling with ice 6: N-bromosuccinmide / N,N-dimethyl acetamide / 0.25 h / 20 °C 7: N,N-dimethyl acetamide / 20 - 60 °C 8: N,N-dimethyl acetamide / 60 - 80 °C 9: ammonia / methanol / 24 h / 90 °C / |Sealed tube View Scheme

1.1: sulfuric acid / 1 h / Inert atmosphere; Reflux 2.1: caesium carbonate; 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene; carbamic acid 1,1-dimethylethyl ester / tris(dibenzylideneacetone)dipalladium(0) chloroform complex / toluene / 90 °C / Inert atmosphere 2.2: 1 h / 20 °C / Inert atmosphere View Scheme

toluene-4-sulfonic acid in methanol

caesium carbonate in N,N-dimethyl-formamide 3 h;

sulfuric acid 1 h; Reflux;

1: LiAlH4 2: CBr4; PPh3 View Scheme