Sulfuryl chloride → HCID 19101393, compound

Participants

Reaction Steps

Sulfuryl chloride (0.9 mL, 0.011 mol) in 5 mL of dichloromethane was added dropwise to a solution of methyl 3,5-dibromo-4-mercaptophenylacetate (3.4 g, 0.11 mol), from Preparation E, in 50 mL dichloromethane. The pale yellow solution was allowed to stand for 1 hour and transferred to an addition funnel. The resulting sulfenyl chloride was then added dropwise to an ice-cooled suspension of 2-isopropylanisole (1.8 g, 0.022 mol) and aluminum chloride (2.8 g, 0.02 mol) in methanol. The reaction mixture was allowed to warm to room temperature and stirred for an additional 15 min. The reaction mixture was then poured on to ice water and extracted twice with dichloromethane. The combined extract was washed with water and brine, dried (Na2SO4), and evaporated on a rotary evaporator. The residue was purified by flash chromatography (silica gel, 5:1 acetone:hexane) to obtain methyl 3,5-dibromo-4-(3-isopropyl-4-methoxyphenylthio)-phenylacetate (3.5 g, 0.007 mol, 70% yield), MP: 73°-76° C.

Provenance & Evidence