3-Bromo-5-ethoxy-4-hydroxybenzaldehyde → 3-Ethoxy-5-formyl-2-hydroxybenzonitrile

HRID 401181Notes

Reaction equation

HRID 401181 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:11][CH2:12][CH3:13])[C:9]=1[OH:10])[CH:5]=[O:6].[Cu][C:15]#[N:16]>CN(C=O)C.O>[CH2:12]([O:11][C:8]1[C:9]([OH:10])=[C:2]([CH:3]=[C:4]([CH:5]=[O:6])[CH:7]=1)[C:15]#[N:16])[CH3:13]

Participants

5

Reactant 2

HCID 6124963-Bromo-5-ethoxy-4-hydroxybenzaldehydeHCID 178418546HCID 178418546, compound

Product 1

HCID 866693323-Ethoxy-5-formyl-2-hydroxybenzonitrileYield 45%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-bromo-5-ethoxy-4-hydroxybenzaldehyde (200 mg, 0.82 mmol) and copper (I) cyanide in DMF (5 mL) was refluxed overnight. The reaction mixture was diluted with water (20 mL), extracted with EtOAc, dried over Na2SO4, and concentrated under reduced pressure. Purified by column chromatography on silica gel to afford Intermediate 51 (70 mg, yield 45%).

Workup

  1. temperaturewas refluxed overnight
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customPurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-6578fea2e0c04fc3949eb5235c47db4e
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

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