454-65-9

Sulfonyl fluoride motif can be used as a connector for the assembly of -SO₂- linked small molecules with proteins or nucleic acids. This new click chemistry approach through sulfates is a complimentary approach to using amides and phosphate groups as linkers.

reaction type: click chemistry

The general procedure for the synthesis of the target compound (CAS: 454-65-9) from 3-bromobenzenesulfonyl chloride was as follows: to a stirred solution of 3-bromobenzenesulfonyl chloride (5 g, 0.0196 mol) in acetonitrile (20 ml) was added potassium fluoride (2.27 g, 0.0391 mol) and 18-crown-6 ether (0.08 g) sequentially and the reaction mixture was stirred at room temperature for for 18 hours. After completion of the reaction, the reaction mixture was washed with water (60 ml) and subsequently extracted with ethyl acetate (3 x 80 ml). The organic extracts were combined and dried with anhydrous sodium sulfate (Na2SO4). Finally, the solvent was evaporated under reduced pressure to give a yellow oily product (3.79 g, 81% yield). The 1H NMR (CDCl3) data of the product were as follows: δ 7.55 (1H, t), 7.92 (1H, d), 7.95 (1H, d), 8.14 (1H, s).

[1] Patent: WO2004/80986, 2004, A1. Location in patent: Page 8
[2] Australian Journal of Chemistry, 1953, vol. 6, p. 318