Isoamyl Nitrite → (2,4-Dibromophenyl)(methyl)sulfane

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A solution of isoamyl nitrite (8.06 mL, 60 mmol) in dimethyl disulfide (36.02 mL, 400 mmol) at 25° C. was slowly treated with 2,4-dibromoaniline (4.8 g, 20 mmol). The reaction was exothermic with gas evolution. The resulting brown reaction mixture was heated to 80-90° C. for 2 h, at which time, thin layer chromatography analysis of the reaction mixture indicated the absence of starting material. The reaction mixture was cooled to 25° C. and then concentrated in vacuo. The resulting residue was dissolved in ethyl acetate (200 mL). The organic layer was washed successively with a 1N aqueous hydrochloric acid solution (1×200 mL) and a saturated aqueous sodium chloride solution (1×200 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. Purification using a plug of silica (Merck Silica gel 60, 230-400 mesh, 4/1 hexanes/ethyl acetate) afforded 2,4-dibromothioanisole (1 1.04 g, 99%) as a brown oil: EI-HRMS m/e calcd for C7H6Br2S (M+) 279.8623, found 279.8619.

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