sodium iodide in acetonitrile 24 h; Heating;

1: 60percent sodium hydride in oil / acetonitrile / 0.5 h / 50 °C 2: 50percent hydrochloric acid / acetonitrile / 0.5 h / 50 °C 3: sodium acetate / H2O / 0.25 h / Heating View Scheme

1: 80 percent / NaI / acetonitrile / 24 h / Heating 2: 1.) 60percent NaH in mineral oil / 1.) DMF, r.t., 0.5 h, 2.) DMF, r.t., 16 h 3: 1.) 60percent NaH in mineral oil, 2.) N-bromosuccinimide / 1.) THF, r.t., 0.5 h, 2.) 0.5 h, r.t. 4: 75 percent / Et3B, O2 / benzene; hexane / 2 h / Ambient temperature 5: 1.) 20percent aq. NaOH, 2.) conc. HCl / 1.) ether, reflux, 24 h, 2.) ethyl acetate, 70 deg C, 4 h View Scheme

sodium hydroxide; tetrabutylammomium bromide in 1,2-dichloro-ethane

sodium hydroxide; tetra-(n-butyl)ammonium iodide 1 h; Heating;