Chemical Properties
White to cream colored powder
Definition
ChEBI: 1H-1lambda~6~-benzo[b]thiophene-1,1-dione is a benzenoid aromatic compound.
Synthesis Reference(s)
Journal of the American Chemical Society, 71, p. 1702, 1949
DOI: 10.1021/ja01173a043
Synthesis
General procedure for the synthesis of benzothiophene sulfone from benzothiophene: 0.15 g (0.0011 mol) of benzothiophene (BT) was placed in a 25 mL round-bottomed flask which was pre-filled with a mixture of 10 mL of toluene/hexane (1:4, v/v) and 0.015 g (0.0135 mmol) of oxidation catalyst. The reaction mixture was heated to 40°C in an oil bath with continuous stirring at 500 rpm. Subsequently, tert-butyl hydroperoxide was added to the reaction system at a molar ratio of oxidizer to substrate of 6.8. The oxidation reaction was carried out under continuous stirring for 6 hours. Upon completion of the reaction, the resulting white benzothiophene sulfone (BTO2) precipitate was collected by filtration and washed with hexane to remove unreacted benzothiophene. The yield was 81%. The 1H NMR (δ, ppm, DMSO-d6) data of the product were as follows: δ 7.83 (d, J = 7.2 Hz, 1H), 7.69 (t, J = 7.4 Hz, 1H), 7.62 (t, J = 9.1 Hz, 3H), 7.34 (d, J = 6.8 Hz, 1H). Elemental analysis results (calculated/measured values, %): C, 57.81/57.49; H, 3.64/3.89; S, 19.29/19.02.
References
[1] Petroleum Chemistry, 2007, vol. 47, # 3, p. 225 - 225
[2] Polyhedron, 2014, vol. 72, p. 19 - 26
[3] RSC Advances, 2014, vol. 4, # 61, p. 32054 - 32062
[4] Patent: CN108658908, 2018, A. Location in patent: Paragraph 0204; 0205
[5] Journal of Organic Chemistry, 1997, vol. 62, # 5, p. 1457 - 1462
