Hydrochloric Acid → 3-(Pentafluoro-lambda6-sulfanyl)aniline

Participants

Reaction Steps

Reduced iron powder (8.60 g) was added to a stirred solution of 3-pentafluorosulphanylnitrobenzene (2.65 g) in a mixture of isopropanol (27 ml), water (6 ml) and concentrated hydrochloric acid (0.3 ml). The resulting mixture was heated under reflux for 1 hour, and was then allowed to cool slightly before being filtered through Hyflo. The Hyflo was washed with more isopropanol, and the combined filtrates were evaporated under reduced pressure. The residue was dissolved in a little diethyl ether and the solution was treated with solid sodium hydrogen carbonate, then dried over magnesium sulphate. After filtration to remove the inorganics the solution was evaporated under reduced pressure, and the oily residue was distilled in a Kugelrohr apparatus. The title compound was collected as a colourless oil, bp 110° C. (oven temperature) at 12 mmHg, which crystallised on standing, yield 1.90 g, mp 32°-35° C.

Provenance & Evidence