Diethyl Ether → 3-Acetyl-4-hydroxybenzonitrile

HRID 991755Notes

Reaction equation

HRID 991755 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8](Br)[CH:7]=[CH:6][C:5]=1[OH:11])=[O:3].[Cu](C#N)[C:13]#[N:14].CCOCC>CN(C=O)C>[C:2]([C:4]1[CH:9]=[C:8]([CH:7]=[CH:6][C:5]=1[OH:11])[C:13]#[N:14])(=[O:3])[CH3:1]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 959915'-Bromo-2'-hydroxyacetophenoneHCID 178418260HCID 178418260, compound

Product 1

HCID 123328323-Acetyl-4-hydroxybenzonitrileYield 70.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

A solution of 5-bromo-2-hydroxyacetophenone (11, 10.00 g, 46.5 mmoles) in anhydrous DMF (25 mL) was mixed with copper cyanide (6.25 g, 69.75 mmoles) and the resulting reaction mixture was heated for about 8 to 16 hours at a temperature of about 160° C. The reaction mixture was cooled to room temperature and mixed with ether, the ether mixture was filtered through celite and the filtrate concentrated to afford a solid which was purified by flash column chromatography through silica using Hexane/EtOAc (4:1) as eluant to yield compound 12 as a clear colorless oil (5.25 g, 70%).

Workup

  1. customthe resulting reaction mixture
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationthe ether mixture was filtered through celite
  4. concentrationthe filtrate concentrated
  5. customto afford a solid which
  6. customwas purified by flash column chromatography through silica

Sources & evidence

ORD record
ord-e78cac6702ce49d98a123b6b1e83b2fa
Source dataset
uspto-grants-2002_10
Patent number
US06465503B2

Reaction notes

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