pyridine; thionyl chloride in dichloromethane

1.1: sodium nitrite; hydrochloric acid / H2O / 1 h / 0 °C 1.2: 46 percent / sodium acetate / H2O / 0 - 20 °C 2.1: lithium aluminum hydride / diethyl ether / 2 h / Heating 2.2: 93 percent / hydrochloric acid; air / diethyl ether 3.1: 76 percent / thionyl chloride; pyridine / CH2Cl2 View Scheme

1.1: lithium aluminum hydride / diethyl ether / 2 h / Heating 1.2: 93 percent / hydrochloric acid; air / diethyl ether 2.1: 76 percent / thionyl chloride; pyridine / CH2Cl2 View Scheme

fluorspar; potassium fluoride in various solvent(s) 85 h; Heating;