Water → 5-Benzoyloxy-3-chloro-2-hydroxy-1-iodobenzene

HRID 497050Notes

Reaction equation

HRID 497050 reaction equation
[C:1]([O:9][C:10]1[CH:11]=[CH:12][C:13]([OH:17])=[C:14]([Cl:16])[CH:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-:18].[Na+].O>CN(C=O)C>[C:1]([O:9][C:10]1[CH:15]=[C:14]([Cl:16])[C:13]([OH:17])=[C:12]([I:18])[CH:11]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5238Sodium IodideHCID 127337475-Benzoyloxy-1-chloro-2-hydroxybenzene

Product 1

HCID 223186275-Benzoyloxy-3-chloro-2-hydroxy-1-iodobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3 g of 5-benzoyloxy-1-chloro-2-hydroxybenzene were dissolved in 35 ml of DMF. 2.17 g of sodium iodide and 3.29 g of chloramin T were added. After one hour of stirring at room temperature, about 500 ml of water were added to the mixture, which was then extracted with ethyl acetate. The organic phase was washed with 5% strength sodium thiosulfate solution, dried and concentrated using a rotary evaporator. The resulting product was clean enough for the next reaction. Yield: 3.81 g (84%)

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washThe organic phase was washed with 5% strength sodium thiosulfate solution
  3. customdried
  4. concentrationconcentrated
  5. customa rotary evaporator
  6. customThe resulting product was clean enough for the next reaction

Sources & evidence

ORD record
ord-4357893131d84d0d83dcf674f1e3b624
Source dataset
uspto-grants-2005_09
Patent number
US06949551B2

Reaction notes

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