Acetyl chloride → 3-Iodophenyl acetate

HRID 985477Notes

Reaction equation

HRID 985477 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[C:9](Cl)(=[O:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:9]([O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([I:1])[CH:3]=1)(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 122723-Iodophenol

Product 1

HCID 131017693-Iodophenyl acetateYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-iodophenol (3 g, 13.6 mmol), acetyl chloride (2.9 ml, 40.9 mmol) and potassium carbonate (9.42 g, 68.2 mmol) in N,N-dimethylformamide (75 ml) was stirred for 16 h at room temperature. The mixture was partitioned between water and ethyl acetate. The organic layer was washed with 1N NaOH, dried over magnesium sulfate, and evaporated under vacuum. The crude product was chromatographed over silica gel, eluting with 20% ethyl acetate/hexanes to yield 2.3 g (65%) of 3-iodophenyl acetate.

Workup

  1. customThe mixture was partitioned between water and ethyl acetate
  2. washThe organic layer was washed with 1N NaOH
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under vacuum
  5. customThe crude product was chromatographed over silica gel
  6. washeluting with 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-84b5c73554c140019667c1bce9a2e921
Source dataset
uspto-grants-2005_03
Patent number
US06872730B2

Reaction notes

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