- Preparation of Phenyl vinyl sulfide
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(CAS no.: ), which is also known as , (ethenylthio)-, could be produced through the following synthetic routes.
A 2-L, three-necked, round-bottomed flask fitted with a reflux condenser, an addition funnel, a magnetic stirring bar, thermometer, and nitrogen inlet is charged with diphenyl disulfide (200 g, 917 mmol) and dichloromethane (320 mL). The addition funnel is charged with bromine (161 g, 52 mL, 1.01 mol). After the diphenyl disulfide dissolves, the nitrogen inlet is replaced with a calcium sulfate-packed drying tube, and the flask is fitted with a gas-dispersion tube. (73.1 g, 2.61 mol) is slowly bubbled into the solution through a gas dispersion tube, and the bromine is added in 2–3-mL portions over 5 hr. After addition of the bromine and ethylene is complete, the drying tube is replaced with the nitrogen inlet, and the flask is fitted with a clean addition funnel. The addition funnel is charged with 1,8-diazabicyclo[5.4.0]undec-7-ene, , (306 g, 300 mL, 2.01 mol). DBU is added at a rate such that the temperature of the reaction mixture does not exceed 55°C. After the DBU is added the reaction mixture is maintained at about 50°C for 15–18 hr. A 1.0 M ammonium hydroxide solution (600 mL) is added to the reaction mixture, and the mixture is transferred to a separatory funnel. The layers are separated, and the aqueous layer is extracted with 300 mL of dichloromethane. The organic fractions are combined, washed with water (600 mL), and dried with 10 g of magnesium sulfate. The mixture is filtered, and the solvent is evaporated under reduced pressure. Distillation of the residue affords 162–184 g (65–74%) of phenyl vinyl sulfide, bp 80–84°C/11–12 mm. The purity is greater than 98% by GC analysis.
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