Sodium Iodide → 2-Iodo-5-nitrophenol

HRID 1040359Notes

Reaction equation

HRID 1040359 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[OH:15].[I-:16].[Na+].S(=O)(O)[O-].[Na+]>O.S(=O)(=O)(O)O.CCOCC.CS(C)=O>[I:16][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[OH:15]

Participants

9

Reactant 4

HCID 5238Sodium IodideHCID 49847212-Amino-5-NitrophenolHCID 23665763Sodium BisulfiteHCID 23668193Sodium Nitrite

Product 1

HCID 186726022-Iodo-5-nitrophenolYield 75.1%

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
5 °C

Procedure

Add, dropwise, a solution of 20.7 g (300 mmol) of sodium nitrite (NaNO2) in 100 mL of water to a solution of 30.81 g (200 mmol) of 2-amino-5-nitrophenol in a mixture of 500 mL of sulphuric acid at 30 wt. % and 500 mL of DMSO cooled to 5° C., maintaining the temperature at 5° C. After 30 min at 5° C., add dropwise a solution of 90 g (600 mmol) of sodium iodide in 100 mL of water, then bring the reaction mixture up to RT. After stirring for 2 h, distribute the reaction mixture in 2 L of a mixture of ether/aqueous solution at 10 wt. % of sodium bisulphite 1:1. Extract the aqueous phase again with 200 mL of ether, combine the organic phases and wash with 3×1 L of water, then dry over Na2SO4. After concentration under reduced pressure, purify the residue obtained by silica gel column chromatography, eluting with a cyclohexane/EtOAc gradient from 0 to 10% of EtOAc. After concentration under reduced pressure, we obtain 39.8 g of 2-iodo-5-nitrophenol in the form of a brown solid.

Workup

  1. additionAdd
  2. temperaturemaintaining the temperature at 5° C
  3. customup to RT
  4. extractionExtract the aqueous phase again with 200 mL of ether
  5. washwash with 3×1 L of water
  6. dry with materialdry over Na2SO4
  7. concentrationAfter concentration under reduced pressure
  8. custompurify the residue
  9. customobtained by silica gel column chromatography
  10. washeluting with a cyclohexane/EtOAc gradient from 0 to 10% of EtOAc
  11. concentrationAfter concentration under reduced pressure, we

Sources & evidence

ORD record
ord-0ad75f6b6abc4691b57a44d33f5f7136
Source dataset
uspto-grants-2013_10
Patent number
US08552201B2

Reaction notes

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