Iodine → HCID 10193055, compound

HRID 1836026Notes

Reaction equation

HRID 1836026 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1.[OH-].[K+].[I:15]I>CO>[I:15][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[C:6]=1[OH:9]

Participants

5

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 15285Phenol, 4-methoxy-2-nitro-

Product 1

HCID 10193055HCID 10193055, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-Methoxy-2-nitrophenol (5 g, 29.6 mmol) in MeOH (100 mL) was cooled to 0° C. and treated with KOH (1.8 g, 32.6 mmol) followed by portionwise addition of I2 (8.2 g, 32.6 mmol). The reaction was worked-up by quenching the excess I2 by adding a 10% Na2SO3 aq solution. The MeOH was stripped off and 2 N HCl aq. was added and the aqueous extracted with EtOAc. The EtOAc was washed with saturated NaHCO3, brine and dried over MgSO4. The solution was concentrated and triturated twice with MeOH to yield 5 g of material that consisted of a 2:1 mixture of product to starting material that was used as is for the next step.

Workup

  1. customby quenching the excess I2
  2. additionby adding a 10% Na2SO3 aq solution
  3. addition2 N HCl aq. was added
  4. extractionthe aqueous extracted with EtOAc
  5. washThe EtOAc was washed with saturated NaHCO3, brine
  6. dry with materialdried over MgSO4
  7. concentrationThe solution was concentrated
  8. customtriturated twice with MeOH

Sources & evidence

ORD record
ord-6c9d3c16b27f44d1aab8201e75dbdb5b
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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