1: 82 percent / diethyl ether / 0.25 h / 0 °C 2: 90 percent / bromine / acetic acid / 3 h / Ambient temperature 3: 22 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / benzene 4: 92 percent / boron tribromide / hexane; CH2Cl2 / 0.5 h / Heating 5: 90 percent / sodium ethoxide / ethanol / 0.5 h / Ambient temperature View Scheme

1: 90 percent / bromine / acetic acid / 3 h / Ambient temperature 2: 22 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / benzene 3: 92 percent / boron tribromide / hexane; CH2Cl2 / 0.5 h / Heating 4: 90 percent / sodium ethoxide / ethanol / 0.5 h / Ambient temperature View Scheme

1: 22 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / benzene 2: 92 percent / boron tribromide / hexane; CH2Cl2 / 0.5 h / Heating 3: 90 percent / sodium ethoxide / ethanol / 0.5 h / Ambient temperature View Scheme

1: 91 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / dimethylformamide / 3 h / -15 °C 2: 82 percent / diethyl ether / 0.25 h / 0 °C 3: 90 percent / bromine / acetic acid / 3 h / Ambient temperature 4: 22 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / benzene 5: 92 percent / boron tribromide / hexane; CH2Cl2 / 0.5 h / Heating 6: 90 percent / sodium ethoxide / ethanol / 0.5 h / Ambient temperature View Scheme

1: N-bromosuccinmide / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere 2: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / 1,4-dioxane / 24 h / 110 °C / Inert atmosphere; Combinatorial reaction / High throughput screening (HTS) 3: boron tribromide / dichloromethane / 12 h / -78 - 20 °C / Inert atmosphere View Scheme

1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / 1,4-dioxane / 24 h / 110 °C / Inert atmosphere; Combinatorial reaction / High throughput screening (HTS) 2: boron tribromide / dichloromethane / 12 h / -78 - 20 °C / Inert atmosphere View Scheme

1: 99 percent / zinc iodide / 0.25 h / 0 °C 2: 2) dil. aq. hydrochloric acid / 1) diethyl ether, reflux, 3 h, 2) 25 deg C, overnight 3: 68 percent / triethylamine / tetrahydrofuran / 0.5 h / 25 °C 4: 91 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / dimethylformamide / 3 h / -15 °C 5: 82 percent / diethyl ether / 0.25 h / 0 °C 6: 90 percent / bromine / acetic acid / 3 h / Ambient temperature 7: 22 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / benzene 8: 92 percent / boron tribromide / hexane; CH2Cl2 / 0.5 h / Heating 9: 90 percent / sodium ethoxide / ethanol / 0.5 h / Ambient temperature View Scheme

diethyl ether; sodium

2: KOH, aq. EtOH View Scheme

1: N2O4 3: KOH, aq. EtOH View Scheme