In a flame-dried round-bottomed flask, 4-bromo-2-chloro-6-methylphenyl diaza-tert-butyl sulfide (4.60 g, 14.4 mmol) was mixed with potassium tert-butanol (16.1 g, 10 equiv). A stirrer was added and operated under nitrogen atmosphere. Subsequently, anhydrous DMSO (50 mL) was added. The reaction mixture was stirred vigorously for 10 minutes at room temperature. Upon completion of the reaction, the mixture was carefully poured into a mixture consisting of crushed ice (150 mL) and 10% hydrochloric acid (74 mL). The resulting suspension was allowed to stand at 4 °C overnight, after which the solid product was collected by filtration and washed with distilled water. After vacuum drying, 2.86 g of beige solid product (86% yield) was obtained. The product was characterized by 1H-NMR (CDCl3, 500 MHz): δ 7.52 (d, J = 1.5 Hz, 1H), 7.82 (d, J = 1.5 Hz, 1H), 8.08 (s, 1H). Mass spectrometry analysis showed a molecular ion peak (MH+) of 230.90.
![Diazene, 1-(4-bromo-2-chloro-6-methylphenyl)-2-[(1,1-dimethylethyl)thio]-, (1E)-](/CAS/20210305/GIF/943145-70-8.gif)
