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

HRID 2178065Notes

Reaction equation

HRID 2178065 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-b03bbee088d84f44a3a3d99238c96040
Source dataset
uspto-grants-2015_06
Patent number
US09067893B2

Reaction notes

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