((2-(2-Iodophenyl)propan-2-yl)oxy)(trifluoromethyl)sulfane

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[1584705-82-7] C10H10F3IOS (MW 361.94) InChI = 1S/C10H10F3IOS/c1-9(2,15-16-10(11,12)13)7-5-3-4-6-8(7)14/h3-6H,1-2H3 InChIKey = OVVURKRTLZQGJM-UHFFFAOYSA-N (electrophilic reagent, radical acceptor) Physical Data: bp 150.6 °C (DSC). Solubility: chloroform, methanol, tetrahydrofuran, dichloromethane. Form Supplied in: clear, colorless liquid; commercially available. Preparative Methods: Method A. 1-3 AgSCF3 (6.9 g, 33.0 mmol) and 1-chloro-1,3-dihydro-3,3-dimethyl-1,2-benziodoxole (9.8 g, 33.0 mmol) were placed into an oven-dried 250 mL Schlenk tube that is equipped with a stirring bar under argon. The tube was quickly sealed with a rubber stopper. The reaction was stirred at 50 °C for 10 min. Thereafter, 150 mL of freshly distilled warm THF was added and the reaction was stirred at 50 °C for 1.0 h. The precipitate (mainly AgCl) was filtered. The solvent was removed under vacuum to give a pale yellow oil. The residue was purified by flash chromatography (Rf = 0.95, petroleum ether), and further purified by Kugelrohr distillation to give 1-trifluoromethylthio-1,3-dihydro-3,3-dimethyl-1,2-benziodoxole (6.1 g, 51% yield) as a colorless oil (eq 1). (1) Method B.4 AgSCF3 (3.5 g, 16.8 mmol) and 1-chloro-1,3-dihydro-3,3-dimethyl-1,2-benziodoxole (5.0 g, 16.8 mmol) were placed into an oven-dried 100 mL Schlenk tube that is equipped with a stirring bar under argon. The tube was quickly sealed with a rubber stopper and the reaction was stirred at 50 °C for 1.0 h. Petroleum ether (100 mL) was then added. The precipitate (mainly AgCl) was filtered. The solvent was removed under vacuum to give a pale yellow oil. The residue was purified by flash chromatography on silica gel (Rf = 0.95, petroleum ether) to give 1-trifluoromethylthio-1,3-dihydro-3,3-dimethyl-1,2-benziodoxole (2.6 g, 43% yield) as a colorless oil (eq 2). (2) Method C.5 A 50-mL round-bottomed flask charged with 2-(2-iodophenyl)propan-2-ol (6.0 mmol), N-trifluoromethylthiosaccharin (2.2 g, 7.8 mmol), and Et3N (1.9 mL, 13.8 mmol) was filled with CH2Cl2 (40.0 mL). The mixture was stirred at room temperature for 5 min. The mixture was concentrated to 10.0 mL. (Caution: The solvent should not be removed completely, which would lead to partial decomposition of the reagent.) The resulting mixture was then purified by flash column chromatography (Rf = 0.95, petroleum ether) to give the product as a colorless liquid (1.8 g, 85% yield) (eq 3). (3) Purity: purified by column chromatography (silica gel and petroleum ether as eluent). Analysis of Reagent Purity: 19F and 1H NMR; elemental analysis. Handing, Storage, and Precaution: The reagent is air and moisture stable. It should be stored at 0–4 °C in a refrigerator.