Iodine → HCID 131733678, compound

HRID 1476699Notes

Reaction equation

HRID 1476699 reaction equation
[I:1]I.C1C=C(Cl)C=C(C(OO)=O)C=1.[S:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25]([OH:28])(=[O:27])=[O:26])=[CH:21][CH:20]=1>ClCCl>[S:25]([C:22]1[CH:23]=[CH:24][C:19]([CH3:29])=[CH:20][CH:21]=1)([O-:28])(=[O:27])=[O:26].[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[I+:1][C:22]1[S:25][CH:19]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 807IodineHCID 6101p-Toluenesulfonic acidHCID 8030ThiopheneHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 131733678HCID 131733678, compoundYield 11.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. customThe solution was evaporated to dryness

Sources & evidence

ORD record
ord-a069d57cc03a42969262bb7e4d60090a
Source dataset
uspto-grants-2016_08
Patent number
US09402397B2

Reaction notes

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