Sodium Iodide → 1-Iodo-4-phenoxybut-2-yne

Participants

Reaction Conditions

Reaction Steps

1.432 ml (2.12 g, 0.0185 mol) of methanesulfonyl chloride was added dropwise to a solution of 2 g of 4-phenoxybut-2-yn-1-ol and 2.77 ml of triethylamine in 30 ml of methylene chloride at such a rate to maintain the reaction temperature at 0° C. After addition, the resulting mixture was stirred for 30 minutes at 0° C. Then the reaction mixture was poured into 30 ml of saturated aqueous sodium bicarbonate solution and extracted with methylene chloride. The organic extracts were dried over sodium sulfate and the solvent removed by evaporation in vacuo and thus crude 4-phenoxy-but-2-yn-1-ol methanesulfonate was obtained. The foregoing crude mesylate was dissolved in 15 ml of acetone and treated with a solution of 5.55 g of sodium iodide and 1.049 g of sodium bicarbonate in 30 ml of acetone. The reaction mixture was stirred for 1 hour at room temperature and then the solvent was removed under reduced pressure. The residue was diluted with water (25 ml) and extracted with methylene chloride, (3×30 ml) the organic extracts were dried and the solvent removed by evaporation. The residue was purified by silica gelcolumn chromatography (50 g) using hexane:ethyl acetate (95:5) as eluant, to yield 2.3 g (62%) of 1-iodo-4-phenoxybut-2-yne. The product was stored in the refrigerator.

Provenance & Evidence