Water → 6-Benzofuranacetonitrile

HRID 1758261Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1758261
Br[CH2:2][C:3]1[CH:11]=[CH:10][C:6]2[CH:7]=[CH:8][O:9][C:5]=2[CH:4]=1.[C-:12]#[N:13].[Na+].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[O:9]1[C:5]2[CH:4]=[C:3]([CH2:2][C:12]#[N:13])[CH:11]=[CH:10][C:6]=2[CH:7]=[CH:8]1

Komponenten

6

Edukt 3

HCID 962WaterHCID 8929Sodium CyanideHCID 2050997979444-77-2

Produkt 1

HCID 126007356-BenzofuranacetonitrileAusbeute 93,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 6-bromomethylbenzofuran (4.38 g, 0.021 mol), sodium cyanide (2.0 g, 0.041 mol), tetrabutylammonium bromide (0.42 g, 0.0013 mol), water (15 cm3) and dichloromethane (15 cm3) was stirred vigorously for 18 hr. The mixture was separated and the organic layer was washed with water, dried (Na2SO4), filtered and the solvent was removed. The residue was extracted with petroleum ether (b.p. 60°-80° C.), and the solvent was removed to give benzofuran-6-acetonitrile (3.09 g, 0.0197 mol), 93.7%) as an oil, t.l.c./silica/toluene, RF 0.21.

Aufarbeitung

  1. customThe mixture was separated
  2. washthe organic layer was washed with water
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent was removed
  6. extractionThe residue was extracted with petroleum ether (b.p. 60°-80° C.)
  7. customthe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-c05139bc217742158e9c12201ca87eb7
Quelldatensatz
uspto-grants-1983_02
Patentnummer
US04372970

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