Trimethylsulfonium iodide → 1-(4-Chloro-2-oxiranyl-phenoxymethyl)-1H-benzotriazole

Participants

Reaction Steps

98 (15.5 g, 54 mmol) is dissolved in 150 ml of DCM and 150 ml of 40% aqueous sodium hydroxide solution. After addition of trimethylsulfonium iodide (14.3 g, 70.2 mmol) and tetrabutylammoniumiodide (1.4 g, 3.8 mmol), the mixture is refluxed for 18 h. The reaction mixture is diluted with DCM, washed with water and the organic layers are dried over Na2SO4. Evaporation gave 18.7 g of a yellow oil, which is further purified by flash-chromatography (silicagel, ethyl acetate/hexanes 3:7)

Provenance & Evidence