aluminium trichloride in carbon disulfide

1: 53 percent / AlCl3 / nitrobenzene / Ambient temperature 2: 53 percent / Zn, HgCl2, conc. HCl / H2O; toluene / 24 h / Heating 3: 81 percent / P2O5, H3PO4 / CH2Cl2 / 0.33 h / 70 - 80 °C 4: 69 percent / Zn / tetrahydrofuran / 2 h 5: 62 percent / Pd-black / 2 h / 280 - 300 °C 6: 1) Mg / 1) Et2O, 30 min 2) Et2O, 3h 7: P2O5, H3PO4 / 0.5 h / 60 - 70 °C 8: 80 percent / pyridinium chlorochromate / CH2Cl2 / 96 h / Ambient temperature 9: 82 percent / NaBH4 / ethanol / 1 h / Ambient temperature 10: 42 percent / CH3SO2Cl, Et3N / CH2Cl2 / 0 °C 11: 77 percent / NaH, EtSH / dimethylformamide / 3 h / 150 °C 12: 57 percent / potassium nitrosodisulfonate, potassium hydrogen phosphate / H2O; acetone / 4 h View Scheme

18-crown-6 ether; potassium bromide in dichloromethane T=0°C; 3.5 h;

18-crown-6 ether; 3-chloro-benzenecarboperoxoic acid; potassium bromide in dichloromethane T=0°C; 0.5 h;

1: 84 percent / KBr, 18-crown-6, m-CPBA / CH2Cl2 / 0.5 h / 0 °C 2: 1) Mg / 1) THF, 2) cooling, then reflux, 5 min 3: 97 percent / NaBH4 / methanol / 0.2 h / 0 °C 4: 98 percent / PBr3, pyridine / benzene / 3 h View Scheme

1: 1.) n-BuLi / 1.) TMEDA, room temperature 2: 90 percent / PBr3 / diethyl ether / 0 °C 3: 99 percent / NaH / tetrahydrofuran / 0 deg C -> room temperature 4: 1.) Ba(OH)2 / 2.) H2O, Et2O, 90 deg C, 17 h 5: LAH / diethyl ether / 0 °C 6: 1.) PBr3, LiBr, collidine, 2.) ZnBr2 / 1.) Et2O, -40 - 0 deg C, 2.) 0 deg C 7: 90 percent / LiH / dimethylformamide / 75 °C 8: SnCl4 / CH2Cl2 / 1.5 h / 0 °C 9: MeSO2Cl, (C2H5)3N / CH2Cl2 / 0 °C 10: m-ClC6H4CO3H / CH2Cl2 / Ambient temperature 11: n-C4H9Li, (i-C3H7)NH / CH2Cl2 / -78 °C View Scheme

n-butyllithium; N,N,N',N,-tetramethylethylenediamine in diethyl ether T=0°C; Yield given;

1: 68 percent / HNO3 / 0 °C 2: 75 percent / Sn, conc. HCl View Scheme

lithium; tert-butyl alcohol in fluessigem NH3 und anschl. mit wss. HCl;

hydrogenchloride; sodium 1) NH3 (liq.), ether, ethanol, reflux, 4 h, then 1 h; 2) ethanol, water, reflux, 1 h; Yield given. Multistep reaction;