- Synthesis of Methyl 2-thienyl sulfide
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Methyl 2-thienyl sulfide (CAS NO.: ), which is known as , 2-(methylthio)-, could be produced through the following synthetic routes.

In a 1-l. three-necked flask fitted with a liquid-sealed mechanical stirrer, a reflux condenser, and a dropping funnel are placed 8 g. (0.33 g. atom) of magnesium turnings and 600 ml. of absolute ether. There is placed in the dropping funnel 70 g. (0.33 mole) of 2-iodothiophene (p.545), the stirrer is started, and about 10 ml. of the iodothiophene is added. The reaction generally begins within a few minutes, and the iodothiophene is then added dropwise at such a rate that moderate refluxing occurs. When the addition is complete, the mixture is refluxed gently until only a small residue of unreacted magnesium remains. The solution is then cooled in an ice bath, the dropping funnel is removed, and 10.7 g. (0.33 g. atom) of finely powdered sulfur is added, the funnel is replaced, and the mixture is refluxed for 45 minutes. The solution is again cooled in an ice bath, and 22.6 ml. (0.36 mole) of methyl iodide is added dropwise from the funnel, and the stirring is then discontinued. The reaction mixture is refluxed 10 hours. It is then cooled, and an aqueous solution of ammonium chloride is run in with vigorous stirring. The liquid is transferred to a separatory funnel, the lower aqueous layer is run off, and the ethereal solution is washed three times with a 2% solution of potassium hydroxide, then with water, and finally is dried over anhydrous sodium sulfate. The ether is removed by distillation at ordinary pressure, and the residual dark liquid is distilled under reduced pressure. The yield of colorless methyl 2-thienyl sulfide is 23–26 g. (53–60%), b.p. 82–86°/22 mm., n25D 1.5978.
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