O-Cresol → 4-Iodo-2-methylphenol

HRID 263495Notes

Reaction equation

HRID 263495 reaction equation
[C:1]1([CH3:8])[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].[I-:10].CC1C=CC(S([N-]Cl)(=O)=O)=CC=1.O.[Na+].O>CN(C=O)C>[I:10][C:3]1[CH:4]=[CH:5][C:6]([OH:7])=[C:1]([CH3:8])[CH:2]=1

Participants

6

Reactant 4

HCID 335O-CresolHCID 962WaterHCID 5238Sodium IodideHCID 16218604Benzenesulfonamide, N-chloro-4-methyl-, sodium salt, monohydrate

Product 1

HCID 1437134-Iodo-2-methylphenolYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 10 g of o-cresol and 16.5 g (1.2 equiv) NaI in 250 ml of DMF was added 31 g (1.2 equiv) of chloramine-T hydrate. The dark green solution was stirred at rt for 1.5 h. The mixture, now a heterogeneous light brown, was poured into water, acidified, extracted with ethyl acetate, and the organic phase washed with water and bisulfite solution. The organic phase was dried over MgSO4. Concentration, trituration with hexane, and flash chromatography (silica gel, hexane, hexane/ethyl acetate (5:1)) provided 13.6 g (63%) of the title compound as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe organic phase washed with water and bisulfite solution
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationConcentration, trituration with hexane, and flash chromatography (silica gel, hexane, hexane/ethyl acetate (5:1))

Sources & evidence

ORD record
ord-ce2ea1557f0747248102c3fba64c305e
Source dataset
uspto-grants-1997_07
Patent number
US05643929

Reaction notes

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