Reaction #792204

Reaction equation

p-Toluene sulfonic acid

Iodine

m-CPBA

thiophene

→

dithienyliodonium tosylate

Yield 11.2%

Solvents

dichloromethane

Conditions

Workup

1. 1
   OtherThe solution was evaporated to dryness

Procedure

Iodine (862 mg, 3.39 mmol), m-CPBA (1.48 g, 8.62 mmol) and thiophene (1 g. 11.88 mmol) were combined in dry dichloromethane (66 mL). p-Toluene sulfonic acid (2.19 g, 11.56 mmol) was added to the solution at room temperature, and the mixture was stirred for 16 hours at room temperature. The solution was evaporated to dryness, and the resulting crude product was subjected to flash chromatography (5-10% MeOH/CH2Cl2)) to yield dithienyliodonium tosylate (11.2%) as a brown colored sticky mass.

Source