Water → (2-Bromophenyl)(p-tolyl)sulfane

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of potassium tert-butoxide (75 g, 0.668 mol, 1.1 eq) in N-methyl-2-pyrrolidone (225 mL) a solution of 4-methylthiophenol (78 g, 0.628 mol, 1.0 eq) dissolved in N-methyl-2-pyrrolidone (225 mL) was added. To the reaction mixture was then added to 1,2-dibromobenzene (73 mL, 605 mol, 1.0 eq); once the addition was complete the reaction mixture was warmed to 100° C. and maintained at this temperature for approximately 22 hrs. (The reaction is monitored by HPLC). After cooling to room temperature water (750 mL) and toluene (375 mL) were added, the phases separated, and the water phase extracted with toluene (250 mL). The organic phases were combined and the organic phase was concentrated by vacuum distillation. Once the distillation was complete, the residue was cooled and methanol (750 mL) added. The solvents were removed from the organic phase by vacuum distillation and further methanol (250 mL) added. Stirring over night at room temperature precipitated 2-(4-tolylsulfanyl)-phenyl bromide which was isolated by filtration, washed with methanol (260 mL) and dried in vacuum. Yield=120.8 g.

Provenance & Evidence