1-Ethynyl-4-(methylsulphonyl)-benzene

Synthesis

To a solution of tetrahydrofuran (450 mL) containing (4-methylsulfonylphenylethynyl)methylsilane (20.7 g, 82.0 mmol) was added tetrabutylammonium fluoride hydrate (8.80 g, 27.3 mmol). The reaction was immediately observed to change from yellow to red color. after 5 min, the reaction was completed and the solvent was subsequently removed under vacuum. Water was added to the residue and the resulting mixture was extracted three times with ethyl acetate. The combined organic layers were washed sequentially with water and brine, dried over magnesium sulfate, filtered and concentrated. The residue was suspended in dichloromethane and the insoluble material was filtered off. The filtrate was concentrated to give the crude product. Purification by fast chromatography (using a RediSep fast column with a silica gel particle size of 230-400 mesh and an eluent of 0-25% ethyl acetate in hexane solution) gave 1-ethynyl-4-methylsulfonylbenzene (10.7 g, 72% yield) as a yellow solid.

References

[1] Journal of Organic Chemistry, 2015, vol. 80, # 21, p. 10939 - 10954
[2] MedChemComm, 2018, vol. 9, # 3, p. 534 - 544
[3] Patent: WO2010/55005, 2010, A1. Location in patent: Page/Page column 107
[4] Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1992, vol. 217, p. 19 - 24
[5] ChemPlusChem, 2015, vol. 80, # 6, p. 938 - 943