Phenol → Phenyl 1H-imidazole-1-sulfonate

HRID 1403722Notes

Reaction equation

HRID 1403722 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:8](N1C=CN=C1)([N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1)(=[O:10])=[O:9].C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1>[N:11]1([S:8]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:10])=[O:9])[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

5

Reactant 3

HCID 996PhenolHCID 10796Cesium carbonateHCID 816091,1'-sulphonylbis-1H-imidazole

Product 1

HCID 90409877Phenyl 1H-imidazole-1-sulfonateYield 60.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of phenol (400 mg, 4.3 mmol) in THF (25 mL) was added 1,1′-sulfonyldiimidazole (1.0 g, 5.1 mmol) and Cs2CO3 (2.8 g, 8.5 mmol). The mixture was stirred at ambient temperature for 16 h. The solvent was removed and the residue was purified by silica gel chromatography to yield the title compound (580 mg, 60%).

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-3d58a4fabebf41b3a136f564eca7e95a
Source dataset
uspto-grants-2014_12
Patent number
US08912219B2

Reaction notes

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