4-Iodoanisole → HCID 22481380, compound

HRID 388194Notes

Reaction equation

HRID 388194 reaction equation
C([O-])(=O)C.C([O-])(=O)C.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([IH+:17])=[CH:13][CH:12]=1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([IH+])=[CH:22][CH:21]=1.O.[S:28]([C:32]1[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=1)([OH:31])(=[O:30])=[O:29].IC1C=CC(OC)=CC=1>C(#N)C>[S:28]([C:32]1[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=1)([O-:31])(=[O:30])=[O:29].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([I+:17][C:23]2[CH:24]=[CH:25][C:20]([O:19][CH3:18])=[CH:21][CH:22]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 696764-IodoanisoleHCID 521998p-Toluenesulfonic acid monohydrateHCID 86652489HCID 86652489, compound

Product 1

HCID 22481380HCID 22481380, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Under N2 protection, 352 mg (1 mmol) p-methoxyphenyliodonium diacetate was dissolved in 1.5 mL of dry acetonitrile. The solution was combined with a solution of 190 mg (1 mmol) tosylic acid monohydrate in 1.5 mL of dry acetonitrile. After addition of 0.11 mL (1 mmol) p-iodoanisole, the mixture was allowed to react at room temperature for 2 hours. The solvent was then removed and the remaining solid was recrystallized from diethylether/dichloromethane to give 422 mg bis(p-methoxyphenyl)iodonium tosylate (82%).

Workup

  1. customto react at room temperature for 2 hours
  2. customThe solvent was then removed
  3. customthe remaining solid was recrystallized from diethylether/dichloromethane

Sources & evidence

ORD record
ord-90725f224eb5420fb898da273a2bcf3c
Source dataset
uspto-grants-2013_02
Patent number
US08377704B2

Reaction notes

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