反应详情

To a solution of 2-fluoro-iodobenzene (267 g, 1.2 mol) in Et3N (6L) was added propargyl alcohol (140 g, 2.5 mol, 2 equiv), followed by PdCl2(dppf) (6.1 g, 8.8 mmol, 0.007 equiv), Ph3P (12.5 g, 47.6 mmol, 0.038 equiv) and copper(I) iodide (12.6 g, 66.3 mmol, 0.053 equiv). The resulting mixture was heated at the reflux temperature for 17 h, allowed to cool to room temperature and filtered through a pad of Celite®. The filtrate was concentrated under reduced pressure and purified by vacuum distillation to give 3-(2-fluorophenyl)prop-2-yn-1-ol (156.6 g, 87%) as a deep brown oil: bp 84° C./0.3 mmHg; TLC (CH2Cl2) Rf 0.44; 1H NMR (CDCl3) δ 2.46 (d, J=5.0 Hz, 1H), 4.45 (d, J=5.0 Hz, 1H), 6.94-7.02 (m, 2H), 7.17-7.23 (m, 1H), 7.31-7.37 (m, 1H); GCMS m/z (rel abundance) 151 (MH+, 75%).

1. temperatureThe resulting mixture was heated at the reflux temperature for 17 h
2. filtrationfiltered through a pad of Celite®
3. concentrationThe filtrate was concentrated under reduced pressure
4. distillationpurified by vacuum distillation