1: 99 percent / aq. K2CO3, n-Bu4NI / tetrahydrofuran 2: 51 percent / Br2 / acetic acid / 60 °C 3: 1.) quinoline, pyridine, 2.) aq. K2CO3, n-Bu4NI / 1.) 160 deg C, 2.) CH2Cl2 4: 74 percent / NH4OAc / acetic acid 5: LiAlH4 / tetrahydrofuran / Heating 6: Et3N / CH2Cl2 7: 28 percent / 1.) Na, NH3, 2.) S2Cl2 / 2.) THF 8: TFA / CHCl3 View Scheme

cupric(II) carbonate; copper (II) hydroxide in methanol T=125°C; 3 h; var. time; also without CO2, other aromatic bromides; MechanismProduct distribution;

1: potassium carbonate / N,N-dimethyl-formamide 2: nitric acid / acetic acid View Scheme

1: potassium carbonate / acetonitrile / 4 h / 20 °C 2: bromine / acetic acid / 60 °C 3: sodium tetrahydroborate / methanol / -20 - 20 °C 4: triethylamine; p-toluenesulfonyl chloride / acetonitrile / Reflux 5: boron tribromide / dichloromethane / 0 - 20 °C View Scheme

1: sodium hydroxide; copper / water / 27 h / |Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 5 h / 100 - 105 °C View Scheme

1: 70 percent / K2CO3 / dimethylformamide / 72 h / Ambient temperature 2: 1.) hydrazine hydrate, 2.) KOH / 1.) diethylene glycol, 100 deg C, 4 5 min, 2.) diethylene glycol, 150 deg C, 3 h View Scheme

1: 95 percent / potassium carbonate / acetone / 20 h / Heating 2: 96 percent / sodium hydride (80percent oil) / tetrahydrofuran / 1.5 h / Heating 3: 1.) magnesium turnings, iodine; 2.) iodomethane / 1.) THF, reflux; 2.) THF, reflux, then r.t. 2 h 4: 100 percent / H2 / palladium-on-carbon / ethanol / Ambient temperature 5: 4.6 g / thionyl chloride / 8 h / Heating 6: CH2Cl2 / Ambient temperature 7: 81 percent / tetrahydrofuran / 15 h / Ambient temperature 8: 1.) hydriodic acid; 2.) hydriodic acid / 1.) glacial acetic acid, reflux, 2 h; 2.) acetic acid, reflux, 7 h 9: 1.) potassium carbonate; 2.) pyridine, dimethylaminopyridine / 1.) DMSO, acetone, r.t., 2 h 10: 75 percent / N-bromosuccinimide, dibenzoylperoxide / CCl4 / 6 h / Heating 11: 1.) sodium borohydride, diphenyl diselenide; 2.) 30percent H2O2 / 1.) ethanol, THF, 2.5 h, reflux; 2.) THF, ethanol, 3 h, 0 deg C View Scheme

1.1: copper; sodium hydroxide / water / Reflux 1.2: Reflux 2.1: sodium carbonate / acetone / 6 h / Reflux 3.1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 80 °C 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 4 h / 20 °C 5.1: sodium hydroxide / methanol / 3 h / 20 °C 6.1: potassium carbonate / acetone View Scheme

1: 83 percent / AlCl3; pyridine / CHCl3 / 24 h / Heating 2: 35 percent / Na2CO3; CuO / dimethylformamide / 4 h / 120 - 130 °C View Scheme

sodium hydroxide