4-Fluorothiophenol

Chemical Properties

Uses

Definition

Synthesis

460-00-4

371-42-6

The general procedure for the synthesis of p-fluorothiophenol from p-bromofluorobenzene is as follows: In a Schlenk tube, pre-dried in an oven, the aryl halide p-bromofluorobenzene (0.5 mmol), sodium thiosulphate (100 mg), cesium carbonate (1 mmol, 325 mg), an appropriate amount of tris(dibenzylideneacetone)dipalladium/palladium acetate, and Xphos ligands were added in turn to the tube and placed in a magnetic stirring chamber. Sub. The Schlenk tube was evacuated and replaced three times with argon, followed by the addition of an appropriate amount of solvent. The reaction mixture was stirred at room temperature until uniformly dispersed. Next, the reaction tube was placed in an oil bath at 80°C and stirred for 24 hours. Upon completion of the reaction, the solids were separated by filtration and washed with ether. Zinc powder (0.5 g) and 10% hydrochloric acid solution (5 mL) were added to the resulting solid under cooling conditions in an ice water bath. After stirring for 1 h, the reaction mixture was extracted with ethyl acetate. The organic layers were combined, washed sequentially with water and saturated saline and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give the crude product of p-fluorothiophenol of satisfactory purity. For part of the relatively stable product, it can be further purified by column chromatography.

References