Water → 2-Hydroxy-1-(2-iodophenyl)ethanone

HRID 2377005Notes

Reaction equation

HRID 2377005 reaction equation
I[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].OC1C(OS(C2C=CC(C)=CC=2)(=O)=O)=C([I:18])C=CC=1.[OH2:30]>CS(C)=O>[OH:30][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[I:18])=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 138307Ethanone, 2-iodo-1-phenyl-HCID 21918218Hydroxy tosyloxy iodobenzene

Product 1

HCID 210994782-Hydroxy-1-(2-iodophenyl)ethanoneYield 12%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 2-iodoacetophenone (1 g, 4.1 mmol) and hydroxy(tosyloxy)iodobenzene (1.86 g, 4.92 mmol) in dimethylsulfoxide:water (40 mL:2 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 40% ethyl acetate/isohexane, to give 2-hydroxy-1-(2-iodophenyl)ethanone (126 mg, 12%). δH (400 MHz, d6 DMSO): 7.94 (1H, dd, J=0.9, 7.8 Hz), 7.54 (1H, dd, J=1.8, 7.7 Hz), 7.49-7.45 (1H, m), 7.25-7.21 (1H, m), 5.37 (1H, t, J=6.0 Hz), 4.52 (2H, d, J=6.0 Hz).

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica
  6. washeluting with 40% ethyl acetate/isohexane

Sources & evidence

ORD record
ord-6acd3799a73b43498eb4b5fc4d1c513a
Source dataset
uspto-grants-2008_12
Patent number
US07468393B2

Reaction notes

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