4-Chloro-2-iodophenol → 5-Chloro-2-hydroxybenzonitrile

HRID 369419Notes

Reaction equation

HRID 369419 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4](I)[CH:3]=1.[Cu](C#N)[C:11]#[N:12]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH:3]=1)[C:11]#[N:12]

Participants

4

Reactant 2

HCID 6202344-Chloro-2-iodophenolHCID 178418260HCID 178418260, compound

Product 1

HCID 27774205-Chloro-2-hydroxybenzonitrileYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-2-iodophenol (85 g, 0.33 mol) was dissolved in 150 ml of DMF, followed by the addition of 32.5 g (0.36 mol) of copper cyanide. The resulting mixture was refluxed for 2 hours and then concentrated under reduced pressure. The residue was dissolved in ethyl acetate, and the thus-prepared solution was washed with water. Subsequent to elimination of an undissolved salt, the solution was concentrated under reduced pressure, whereby 40.4 g of 5-chloro-2-hydroxybenzonitrile were obtained (yield: 80%). Without purification, it was provided for use in the next step.

Workup

  1. temperatureThe resulting mixture was refluxed for 2 hours
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe thus-prepared solution was washed with water
  5. concentrationSubsequent to elimination of an undissolved salt, the solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f3352d88e25148b4acc039e8361129c1
Source dataset
uspto-grants-2000_10
Patent number
US06136848

Reaction notes

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