1: COCl2, DMF / CH2Cl2 / Ambient temperature 2: CH2Cl2 / Ambient temperature 3: SOCl2 / CHCl3 / Ambient temperature View Scheme

1: CH2Cl2 / Ambient temperature 2: SOCl2 / CHCl3 / Ambient temperature View Scheme

1: 1.) LDA, 2.) 1,2-dibromotetrafluoroethane / 1.) THF, -78 deg C, 1 h, 2.) THF, from -78 deg C to RT 2: 45 percent / 4.5 M aq. HCl / 6 h / Heating View Scheme

1: 1.) LDA, 2.) 1,2-dibromotetrafluoroethane / 1.) THF, -78 deg C, 1 h, 2.) THF, from -78 deg C to RT 2: 45 percent / 4.5 M aq. HCl / 6 h / Heating 3: (COCl)2, DMF / CH2Cl2 / 18 h / Ambient temperature 4: 1.) isopropylmagnesium chloride / 1.) THF, -78 deg C, 30 min, 2.) THF, from -78 deg C to RT View Scheme

1.1: lithium diisopropylamide / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 93 percent / various solvent(s) / -78 - 20 °C 2.1: 92 percent / hydrochloric acid / H2O / 8 h / Heating View Scheme

1: 1) lithium diisopropylamide / 1) THF, -78 deg C, 30 min, 2) up to room temp. 2: 1) lithium diisopropylamide / 1) THF, 0 deg C, 30 min, 2) up to room temp. 3: 99 percent / CsF, H2O / dimethylformamide / Ambient temperature 4: 61 percent / 6 N HCl / Heating View Scheme

n-butyllithium; diisopropylamine in tetrahydrofuran; water

1,1,1,3,3,3-hexachloro-propan-2-one; lithium diisopropyl amide 1) THF, -78 deg C, 2) up to room temp.; Yield given. Multistep reaction;

1: 1) lithium diisopropylamide / 1) THF, -78 deg C, 30 min, 2) up to room temp. 2: 1) lithium diisopropylamide / 1) THF, 0 deg C, 30 min, 2) up to room temp. 3: 99 percent / CsF, H2O / dimethylformamide / Ambient temperature 4: 61 percent / 6 N HCl / Heating 5: COCl2, DMF / CH2Cl2 / 2 h / Ambient temperature 6: 1) n-BuLi, bipyridyl / 1) THF, -35 -> -5 deg C, 2) THF, -78 deg C, 1 h 7: 98 percent / acetic anhydride / 3 h / Heating 8: ethanol / a) 5 - 15 deg C, 90 min, b) 2 h , room temp. 9: 1) 60percent NaH, 2) 6 M HCl / 1) THF, room temp., 2) reflux, 3 h View Scheme