4-(3,5-Dimethyl-benzylsulfanyl)-nitrobenzene → 4-(3,5-Dimethyl-benzylsulfanyl)-phenylamine

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Reaction Steps

A mixture of 4-(3,5-dimethyl-benzylsulfanyl)-nitrobenzene (0.35 g, 1.28 mmol) calcium chloride (0.071 g, 0.64 mmol) and iron powder (−325 mesh) (0.573 g, 10.3 mmol) in 4 ml water and 17 ml ethanol was heated at reflux under nitrogen for 4.5 h. The reaction mixture was then cooled to room temperature, filtered through Celite and the filtrate was concentrated under reduced pressure. The residual oil was purified by column chromatography, eluting with 9:1 hexane/ethyl acetate to yield the title compound as a yellowish oil (0.29 g, 91% yield). MS: 244.3 (M+1)

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