1: 98 percent / 1 h / Heating 2: 84 percent / sodium hydride / dimethylformamide / 0.67 h / 30 °C 3: 91 percent / pyridine hydrochloride / 2 h / 180 °C 4: K2CO3 / dimethylformamide / 1.) 60 deg C, 2 h, 2.) from 60 deg C to RT, overnight 5: 63 percent / 5percent aq. NaOH / ethanol / 0.5 h / Heating View Scheme

1: 84 percent / sodium hydride / dimethylformamide / 0.67 h / 30 °C 2: 91 percent / pyridine hydrochloride / 2 h / 180 °C 3: K2CO3 / dimethylformamide / 1.) 60 deg C, 2 h, 2.) from 60 deg C to RT, overnight 4: 63 percent / 5percent aq. NaOH / ethanol / 0.5 h / Heating View Scheme

1: 1.) 2.2 M n-butyllithium, 2.) hexachloroethane / 1.) Et2O, reflux, 2.5 h, 2.) Et2O, THF, form -65 deg C to RT 2: 67 percent / AlCl3 / 1,2-dichloro-ethane / 1.) from 5 deg C to RT, 30 min, 2.) reflux, 30 min 3: 76 percent / hydroxylamine hydrochloride, pyridine / 24 h / Heating 4: 98 percent / 1 h / Heating 5: 84 percent / sodium hydride / dimethylformamide / 0.67 h / 30 °C 6: 91 percent / pyridine hydrochloride / 2 h / 180 °C 7: K2CO3 / dimethylformamide / 1.) 60 deg C, 2 h, 2.) from 60 deg C to RT, overnight 8: 63 percent / 5percent aq. NaOH / ethanol / 0.5 h / Heating View Scheme