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

HRID 1034434Notes

Reaction equation

HRID 1034434 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.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[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

6

Reactant 2

HCID 80711,2-DimethoxyethaneHCID 162722-Bromobenzonitrile

Product 1

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

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Intermediate 1 (20 g) was added to a stirred solution of 2-bromobenzonitrile (10.34 g) and tetrakis(triphenylphosphine)palladium (0) (1.5 g) in DME (200 ml) and 8% NaHCO3 (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. T.l.c. System A (1:9), Rf 0.45.

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-5ac042d5f1f74c62a73b662558f2ab18
Source dataset
uspto-grants-1994_05
Patent number
US05317023

Reaction notes

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