Methanol → 3-Cyano-5-iodobenzoic acid

HRID 431860Notes

Reaction equation

HRID 431860 reaction equation
C[O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([I:10])[CH:7]=[C:6]([C:11]#[N:12])[CH:5]=1.[Li+].[OH-].CO>O1CCCC1>[C:11]([C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([I:10])[CH:7]=1)[C:3]([OH:13])=[O:2])#[N:12]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 21942623Methyl 3-cyano-5-iodobenzoate

Product 1

HCID 219426613-Cyano-5-iodobenzoic acidYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl-3-cyano-5-iodobenzoate (640 mg, 2.3 mmol) in tetrahydrofuran (8 mL) was treated with 0.5M LiOH (5.5 mL, 2.75 mmol) and methanol. The reaction mixture was heated at reflux for 1 hour. The solvent was concentrated in vacuo and the mixture treated with 1N HCl. The resulting white precipitate was filtered and the filtrate was extracted with dichloromethane. The residue and the extracted filtrate were combined and concentrated in vacuo to afford 590 mg (94%) of 3-cyano-5-iodobenzoic acid, as a white solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1 hour
  3. concentrationThe solvent was concentrated in vacuo
  4. additionthe mixture treated with 1N HCl
  5. filtrationThe resulting white precipitate was filtered
  6. extractionthe filtrate was extracted with dichloromethane
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-43e72154a7d94096ab505a130f11a08d
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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