1,2-Dimethoxyethane → 2-(5-Methylbenzofuran-2-yl)benzonitrile

HRID 1656025Notes

Reaction equation

HRID 1656025 reaction equation
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].CO[CH2:12][CH2:13][O:14][CH3:15]>C([O-])(O)=O.[Na+].CCOCC>[CH3:6][C:3]1[CH:4]=[CH:12][C:13]2[O:14][C:15]([C:2]3[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=3[C:4]#[N:5])=[CH:8][C:9]=2[CH:2]=1

Participants

5

Reactant 2

HCID 80711,2-DimethoxyethaneHCID 162722-Bromobenzonitrile

Product 1

HCID 156808442-(5-Methylbenzofuran-2-yl)benzonitrile

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Intermediate 1 (20 g) was added to a stirred solution of 2-bromobenzonitrile (10.34 g) and tetrakistriphenylphosphine palladium (0) (1.5 g) in DME (200 ml) and 8% NaHCO3 solution (50 ml) at reflux under nitrogen. Further catalyst (1.5 g) was added and the reaction continued overnight. The reaction was cooled to room temperature and diluted with ether (200 ml). The organic layer was separated, washed with water (3×100 ml) and dried. Filtration and evaporation gave a white solid which was purified by chromatography eluting with system A (1:9) to give the title compound (10.58 g) as a white solid.

Workup

  1. temperatureat reflux under nitrogen
  2. customthe reaction continued overnight
  3. customThe organic layer was separated
  4. washwashed with water (3×100 ml)
  5. customdried
  6. filtrationFiltration and evaporation
  7. customgave a white solid which
  8. customwas purified by chromatography
  9. washeluting with system A (1:9)

Sources & evidence

ORD record
ord-fa079851bdcb45eb86b1eb4b6fc0ab01
Source dataset
uspto-grants-1993_10
Patent number
US05252593

Reaction notes

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