Ethyl 4-hydroxy-3-iodobenzoate → Ethyl 3-cyano-4-hydroxybenzoate

HRID 420821Notes

Reaction equation

HRID 420821 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1I.[C:14]([Cu])#[N:15]>CS(C)=O>[C:14]([C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:2]=1[OH:1])[C:6]([O:8][CH2:9][CH3:10])=[O:7])#[N:15]

Participants

4

Reactant 2

HCID 11220038Ethyl 4-hydroxy-3-iodobenzoateHCID 178418546HCID 178418546, compound

Product 1

HCID 21322395Ethyl 3-cyano-4-hydroxybenzoateYield 76%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

Dissolve ethyl 4-hydroxy-3-iodo-benzoate (45 g, 154.1 mmoles) in DMSO (125 mL). Add CuCN (15.17 g, 169.5 mmoles). Stir the mixture at 100° C. overnight. After cooling, pour the mixture into ice/water. Filter the solid obtained, wash with water and dry under reduced pressure. Dissolve the solid in EtOAc. Filter through Celite®. Dry over MgSO4 and remove the solvent to obtain 22.36 g of ethyl 3-cyano-4-hydroxy-benzoate (76% yield). MS(ES): m/z=190.0 [M-H].

Workup

  1. temperatureAfter cooling
  2. filtrationFilter the solid
  3. customobtained
  4. washwash with water
  5. customdry under reduced pressure
  6. dissolutionDissolve the solid in EtOAc
  7. filtrationFilter through Celite®
  8. dry with materialDry over MgSO4
  9. customremove the solvent

Sources & evidence

ORD record
ord-c0263a296f6046a988f7b1e82a495214
Source dataset
uspto-grants-2012_01
Patent number
US08097652B2

Reaction notes

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