To a stirred solution of 2-bromoethanol (11.78 mL, 165.92 mmol, 7.0 equiv) in acetonitrile (68 mL) was added potassium carbonate (9.8 g, 71.10 mmol, 3.0 equiv). The reaction mixture was stirred at room temperature for 30 minutes before thiomorpholine-1,1 -dioxide (3.2 g, 23.70 mmol, 1.0 eq.) was added. The reaction mixture was heated to reflux and stirred overnight. The progress of the reaction was monitored by thin layer chromatography (TLC) to confirm that the feedstock was completely consumed and the target product was generated. Upon completion of the reaction, the mixture was cooled to room temperature and filtered. The filtrate was concentrated to obtain the crude product, which was subsequently purified by column chromatography using a mixture of dichloromethane and 3% methanol as eluent, resulting in 4-(2-hydroxyethyl)thiomorpholine-1,1-dioxide (2.5 g, 60.0% yield) as a brown liquid. The product was characterized by 1H NMR (DMSO-d6, 300 MHz): δ 4.50 (t, 1H), 3.51 (q, 2H), 3.07 (m, 4H), 2.95 (m, 4H), 2.58 (t, 2H); Mass Spectrometry (MS): [M + H]+ m/z 180.19 (10%).
