2,6-Lutidine → 4-[[2-(Methoxymethoxy)benzyl]sulfanyl]aniline

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Reaction Steps

2-(methoxymethoxy)benzylalcohol (8.0 g) was dissolved in THF, 2,6-dimethylpyridine (8.3 ml) and methanesulfonic acid anhydride (9.9 g) were added to the mixture, and the mixture was stirred at room temperature for 3 hours. Lithium bromide (5.8 g) was added to the mixture, the mixture was stirred for 4 hours at room temperature and the mixture was further stirred for 20 hours at 50° C. After allowing the mixture to be cooled to room temperature, water was added to the mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was added dropwise to an aqueous solution (104 ml) of 4-aminothiophenol (4.2 g) and sodium hydroxide (2.0 g) in methanol, and the mixture was stirred for 12 hours at room temperature. The solvent was removed under reduced pressure, and water was added to the obtained residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give 4-[[2-(methoxymethoxy)benzyl]sulfanyl]aniline (8.2 g).

Provenance & Evidence