in N,N-dimethyl-formamide T=150°C;

1: 99 percent / n-butyllihium / hexane; diethyl ether / 0.75 h / -78 °C 2: 98 percent / pyridine, chromium (VI) oxide / CH2Cl2 / 0.75 h / Ambient temperature 3: 98 percent / hydrogen / 20percent Pd/C / methanol / 15 h / 760 Torr / Ambient temperature 4: 92 percent / N,N-diisopropylethylamine / CH2Cl2 / 17 h / Ambient temperature 5: 51 percent / lithium diisopropylamide, N,N,N',N'-tetramethylethylenediamine / tetrahydrofuran; hexane / 2 h / -78 °C 6: 42 percent / 2.6 M Jones reagent, celite / acetone / 0.33 h / Ambient temperature 7: 67 percent / 38percent ammonia / H2O; tetrahydrofuran / 15 h / Ambient temperature 8: 93 percent / sodium borohydride, 37percent hydrochloric acid / methanol; H2O / 2 h / 0 °C 9: 85 percent / pyridine / 15 h / Ambient temperature 10: 86 percent / ferric chloride on silica gel / CHCl3 / 15 h / Ambient temperature 11: sodium periodate / methanol; H2O / 12 h / Ambient temperature 12: NaBH4 / methanol; H2O / 0.5 h / Ambient temperature 13: 91 percent / pyridine, 4-dimethylaminopyridine / 12 h / Ambient temperature 14: 82 percent / hydrogen / 10percent Pd/C / ethyl acetate / 5 h / Ambient temperature 15: 99 percent / dimethyl sulfoxide, oxalyl chloride / CH2Cl2 / 0.25 h / -78 °C 16: zinc powder, acetic acid / tetrahydrofuran; H2O / 30 h / Ambient temperature 17: zinc chloride / CH2Cl2 / 0.17 h / Ambient temperature 18: 81 percent / trifluoroacetic acid / CH2Cl2 / 5 h / Ambient temperature 19: 68 percent / N,N-diisopropylethylamine / acetonitrile / 3 h / 60 °C 20: 79 percent / 2.6 M Jones reagent, celite / acetone / 0.5 h / Ambient temperature 21: 88 percent / sodium hydroxide / methanol / 2 h / Ambient temperature 22: 81 percent / silver nitrate / methanol / 1 h / Ambient temperature View Scheme

tetrachloromethane; bromine Irradiation.unter Belichtung, Erwaermen des erhaltenen 2-Brom-3-dibrommethyl-aniols mit Morpholin und Behandeln des Reaktionsprodukts mit wss. HCl;

diethyl ether; magnesium anschliessendes Behandeln mit CO2;

(i) nBuLi, (ii) /BRN= 1900390/; Multistep reaction;

暂无反应条件数据

boron tribromide in dichloromethane T=-60 - 20°C; 121 h;

1: With hydrogen bromide; sodium nitrite in water T=0 - 5°C; 2: With copper(I) bromide in water T=0 - 70°C; Sandmeyer Reaction; 1.75 h;

potassium hydroxide in acetonitrile T=24°C; Inert atmosphere;

1: H2 / PtO2 / propan-2-ol / 2327.2 Torr 2: 1) conc. H2SO4, NaNO2, 2) CuBr, HBr / 1) H2O, 0-10 deg C, 2) H2O View Scheme