Thiophenol → 3-Chloropropyl phenyl sulfide

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Reaction Steps

6.0 g of thiophenol and 7.8 g of 3-bromo-1-chloropropane were placed in 40 ml of water, and the resultant solution was subjected to reflux for 1 hour under heating. Then, 40 ml of an aqueous solution containing 2.4 g of sodium hydroxide were fed dropwise to the solution. The solution was then further subjected to reflux for another 2 hours under heating. The solution reacted was then poured into ice-water and extracted with ethyl acetate. The ethyl acetate layer resulted was then washed with dilute aqueous alkaline solution and saturated saline solution in series, and the organic layer resulted was dried with anhydrous magnesium sulfate. The solvent used was removed by distillation under reduced pressure, and the residue obtained was then purified by using silica gel column chromatography, for which hexane was used for the developer, thereby affording 6.5 g of 1-chloro-3-phenylthio propane.

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