Water → 6-Benzofuranacetonitrile

HRID 1758261Notes

Reaction equation

HRID 1758261 reaction equation
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

Participants

6

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 2050997979444-77-2

Product 1

HCID 126007356-BenzofuranacetonitrileYield 93.8%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c05139bc217742158e9c12201ca87eb7
Source dataset
uspto-grants-1983_02
Patent number
US04372970

Reaction notes

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