Iodine → HCID 131733678, compound

HRID 705022Notes

Reaction equation

HRID 705022 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-871b85e493584f6887bef425002d4e5f
Source dataset
uspto-grants-2015_11
Patent number
US09173401B2

Reaction notes

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