Chemical Properties
White to off-white crystalline powder
Synthesis
Sodium metal (9.3 g, 0.18 mol) was added to a degassed solution of anhydrous DMF (105 mL) of 2-methyl-2-propanethiol (20.9 mL, 0.18 mol) in batches under nitrogen protection at 0 °C, with stirring maintained. After the mixture was allowed to warm up naturally to room temperature (20-25 °C), stirring was continued for 12 hours. Subsequently, 1,2,4,5-tetrachlorobenzene (8.0 g, 0.037 mol) was added to the reaction system and stirred at room temperature for 2 h. The reaction was maintained for 18 h. After the reaction was completed, the mixture was slowly warmed to reflux. After completion of the reaction, cooled to room temperature, the reaction mixture was poured into ice water (100 g), the precipitated solid was separated by filtration, washed with water and dried to give 1,2,4,5-tetrakis(tert-butylsulfanyl)benzene (11.0 g), the product was an off-white powder. The product was characterized as follows: 1H NMR (600 MHz, CDCl3): δ 1.36 (s, 36H), 7.94 (s, 2H); 13C NMR (150 MHz, CDCl3): δ 31.4, 48.3, 139.5, 144.9; MS (ESI): [M + H]+ 430.7 (Observed), 431.2 (calculated). values).
References
[1] Journal of Organic Chemistry, 2006, vol. 71, # 19, p. 7268 - 7279
[2] The Journal of organic chemistry, 2002, vol. 67, # 14, p. 4635 - 4639
[3] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 24, p. 6801 - 6805
[4] Synthetic Communications, 2013, vol. 43, # 10, p. 1447 - 1454
[5] European Journal of Organic Chemistry, 2014, vol. 2014, # 36, p. 8077 - 8084
