Ethyl Acetate → 3-Ethoxy-5-formyl-2-hydroxybenzonitrile

HRID 401171Notes

Reaction equation

HRID 401171 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:14][CH2:15][CH3:16])[C:9]=1[O:10]COC)[CH:5]=[O:6].[C:17]([Cu])#[N:18].CCOC(C)=O>CN(C=O)C>[CH2:15]([O:14][C:8]1[C:9]([OH:10])=[C:2]([CH:3]=[C:4]([CH:5]=[O:6])[CH:7]=1)[C:17]#[N:18])[CH3:16]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 653644473-Bromo-5-ethoxy-4-(methoxymethoxy)benzaldehydeHCID 178418546HCID 178418546, compound

Product 1

HCID 866693323-Ethoxy-5-formyl-2-hydroxybenzonitrileYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 3-bromo-5-ethoxy-4-(methoxymethoxy)benzaldehyde (600 mg, 2.1 mmol) and CuCN (280 mg, 3.1 mmol) in DMF (10 mL) was heated at 180° C. for 4 hours. TLC (PE:EtOAc=1:1) indicated that the most of the starting material was consumed. The solvent was removed in vacuo, and the residue was purified by column chromatography to afford the 3-ethoxy-5-formyl-2-hydroxybenzonitrile (200 mg, yield: 50.0%).

Workup

  1. customwas consumed
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-4549b7a52959456da422b67e65105241
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

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