Water → 5-Cyano-2-isopropoxy-benzaldehyde

HRID 1290010Notes

Reaction equation

HRID 1290010 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:10][CH:11]([CH3:13])[CH3:12])=[C:6]([CH:9]=1)[CH:7]=[O:8].[Cu][C:15]#[N:16].CN(C=O)C.O>C(OCC)(=O)C>[C:15]([C:2]1[CH:3]=[CH:4][C:5]([O:10][CH:11]([CH3:13])[CH3:12])=[C:6]([CH:9]=1)[CH:7]=[O:8])#[N:16]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 8199735-Bromo-2-isopropoxybenzaldehydeHCID 178418546HCID 178418546, compound

Product 1

HCID 189223515-Cyano-2-isopropoxy-benzaldehyde

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared by the treatment of 5-bromo-2-isopropoxy-benzaldehyde (3.5 gm, 0.014 mol) with copper(I) cyanide (2.5 gm, 0.028 mol) in refluxing DMF for 28 hours. The cooled mixture was poured into a mixture of water (100 mL) and ethyl acetate (100 mL). The mixture was filtered through a pad of Celite, the organic layer separated, washed with saturated brine solution, dried (Na2SO4), and evaporated. The title compound was purified by flash chromatography eluting with 15% ethyl acetate in hexane; yield 1.9 gm of a white solid.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. customthe organic layer separated
  3. washwashed with saturated brine solution
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe title compound was purified by flash chromatography
  7. washeluting with 15% ethyl acetate in hexane

Sources & evidence

ORD record
ord-349a563f115b48d68ce4c334d03afeef
Source dataset
uspto-grants-1998_05
Patent number
US05750549

Reaction notes

Loading…