2-Bromobenzonitrile → 2-(5-Methylbenzofuran-2-yl)benzonitrile

HRID 1729491Notes

Reaction equation

HRID 1729491 reaction equation
Br[C:2]1[C:6]2[CH:7]=[C:8]([CH2:11]Br)[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1NC(=O)OC(C)(C)C.BrC1C=CC=CC=1[C:30]#[N:31]>COCCOC.C([O-])(O)=O.[Na+].CCOCC>[CH3:11][C:8]1[CH:9]=[CH:10][C:5]2[O:4][C:3]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:30]#[N:31])=[CH:2][C:6]=2[CH:7]=1

Participants

6

Reactant 2

HCID 162722-BromobenzonitrileHCID 117549251,1-Dimethylethyl [2-[3-bromo-5-(bromomethyl)-2-benzofuranyl]phenyl]carbamate

Product 1

HCID 156808442-(5-Methylbenzofuran-2-yl)benzonitrileYield 109.1%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 80711,2-DimethoxyethaneSolventHCID 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% aqueous NaHCO3 (50 ml) at reflux under nitrogen. Further catalyst (1.5 g) was added and the reaction was heated 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. temperaturethe reaction was heated 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-0b841245bf3842869ae0be7e4ca9ffb2
Source dataset
uspto-grants-1994_07
Patent number
US05332831

Reaction notes

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