sodium iodide in acetonitrile 24 h; Heating;

1: 75 percent 2: 51 percent / NaI / acetonitrile / 48 h / Heating View Scheme

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