n-butyllithium; nitryl chloride 1) hexane, ether, 3 d, r.t., 2) -196 deg C to -95 deg C, 10 min; -90 deg C to 70 degC, 2 h; -70 drg C to r.t., 1.5 h; Yield given. Multistep reaction. Yields of byproduct given;

titanium tetrachloride in dichloromethane T=0°C; 1 h;

1: 67 percent / AlCl3 / 1,2-dichloro-ethane / 1.) from 5 deg C to RT, 30 min, 2.) reflux, 30 min 2: 76 percent / hydroxylamine hydrochloride, pyridine / 24 h / Heating 3: 98 percent / 1 h / Heating 4: 84 percent / sodium hydride / dimethylformamide / 0.67 h / 30 °C 5: 91 percent / pyridine hydrochloride / 2 h / 180 °C 6: K2CO3 / dimethylformamide / 1.) 60 deg C, 2 h, 2.) from 60 deg C to RT, overnight 7: 63 percent / 5percent aq. NaOH / ethanol / 0.5 h / Heating View Scheme

1: 79 percent / TiCl4 / CH2Cl2 / 1 h / 0 °C 2: 74 percent / BBr3 / CH2Cl2 / 1 h / 0 °C 3: 79.6 percent / K2CO3 / butan-2-one / 4.5 h / Heating 4: 82.9 percent / H2, conc.H2SO4 / 20percent Pd/C / acetic acid / 2 h / 2280 Torr 5: LiCl, Me2SO, H2O / 2 h / Heating 6: H2SO4 / Ambient temperature 7: 69.2 percent / AlCl3 / 1,2-dichloro-ethane / 3.75 h / 5 - 20 °C 8: 20 percent / NH2OH*HCl, pyridine / 4 h / Heating 9: 58 percent / 1 h / 90 °C 10: NaH / dimethylformamide / 4 h / Ambient temperature 11: 92 percent / aq. KOH / methanol / 1 h View Scheme