Benzyl Bromide → 3-(Benzylsulfanyl)aniline

Participants

Reaction Steps

To a stirring suspension of 25 grams (0.20 mole; M.W. 125.19) of 3-aminothiophenol in 200 ml. of 5N NaOH was added dropwise a solution of 34.2 grams of α-bromotoluene (0.20 mole; M.W. 171.04) dissolved in 100 ml. of 1,4-dioxane. The addition required about 30 minutes. The reaction mixture was stirred at room temperature for 2 hours and then extracted with two 500 ml. portions of ethyl ether. The extracts were combined, dried over Na2SO4, and evaporated to yield 41.0 grams of m-benzylthioaniline.

Provenance & Evidence