Sulfonium, (Fluoromethyl)phenyl(2,3,4,5‐tetramethylphenyl)‐, Tetrafluoroborate(1‐) (1:1) 1

Abstract

[1009088-40-7] C17H20BF5S (MW 362.22) InChI = 1S/C17H20FS.BF4/c1-12-10-17(15(4)14(3)13(12)2)19(11-18)16-8-6-5-7-9-16;2-1(3,4)5/h5-10H,11H2,1-4H3;/q+1;-1 InChIKey = SDWOHFZFPMIYRL-UHFFFAOYSA-N Alternative Name(s): S-monofluoromethyl-S-phenyl-2,3,4,5-tetramethylphenylsulfonium tetrafluoroborate, STBF4. Physical Data: mp 118–121 °C. Solubility: soluble in dichloromethane, chloroform, dimethylformamide, and acetonitrile; partially soluble in THF (upon standing solvent polymerization observed); and insoluble in water, diethyl ether, and petroleum ether. Form Obtained in: white or light brown solid; commercially available. Analysis of Reagent Purity: 1H NMR (400 MHz, CDCl3) δ 7.77 (m, 2H), 7.76–7.69 (m, 1H), 7.66 (m, 2H), 7.43 (s, 1H), 6.55 (dd, J = 46.6, 9.6 Hz, 1H), 6.42 (dd, J = 45.6, 9.5 Hz, 1H), 2.49 (s, 3H), 2.38 (s, 3H), 2.30 (s, 3H), 2.28 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 143.9, 139.4, 138.2, 137.4, 134.3, 131.4, 130.8, 128.4 (d, J = 4.6 Hz), 121.2 (d, J = 2.7 Hz), 116.2, 89.6 (d, J = 241.7 Hz), 21.1, 17.7, 16.9, 16.8. 19F NMR (376 MHz, CDCl3) δ −151.45, −151.51, −207.18 (t, J = 46.4 Hz). Preparative Method: prepared in a four-step process starting from sodium phenyl thiolate, phenyl sulfoxide, or thioanisole. Purification: extraction between dichloromethane and water, silica gel chromatography (eluent gradient CH2Cl2, then CH2Cl2/MeCN 1:1), or/and washing precipitate with petroleum ether/diethyl ether. Handling, Storage, and Precautions: bench stable and can be stored more than one year at room temperature. No information is currently available in terms of the reagent's effect on health.