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

HRID 924970Notes

Reaction equation

HRID 924970 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-1b361a11b33642ae9648e5cf616e853d
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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