Uses
4-(Methylthio)benzaldehyde is a building block for the synthesis of various pharmaceutical and biologically active compounds. It can be used for the synthesis of sulfur-containing terpyridine ligands. It is the intermediate for the synthesis of a class of pyrrole derivatives showing analgesic/anti-inflammatory activity.
Synthesis
In the standard synthetic method, diphenyl sulfoxide (2.2 g, 0.01 mol) is mixed with brominated silica (18.18 g, 40 mmol Br/g silica) in a nonprotonic solvent such as dichloromethane (2 mL) or carbon tetrachloride. The reaction was carried out at room temperature while atmospheric water needed to be removed for 5 min. Upon completion of the reaction, the product was separated by simple filtration, followed by evaporation of the solvent to give diphenyl sulfide in its pure state (yield 1.84 g, 99%).
References
[1] Synthetic Communications, 2007, vol. 37, # 22, p. 4079 - 4083
[2] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 8, p. 2525 - 2526
[3] Tetrahedron Letters, 2009, vol. 50, # 49, p. 6872 - 6876
[4] Journal of Sulfur Chemistry, 2014, vol. 35, # 1, p. 7 - 13
[5] Journal of Sulfur Chemistry, 2017, vol. 38, # 6, p. 597 - 603
