Sodium hydride → 6-Bromo-3-benzofuranacetonitrile

HRID 1459415Notes

Reaction equation

HRID 1459415 reaction equation
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[Br:14][C:15]1[CH:24]=[CH:23][C:18]2[C:19](=O)[CH2:20][O:21][C:17]=2[CH:16]=1>C1COCC1>[Br:14][C:15]1[CH:24]=[CH:23][C:18]2[C:19]([CH2:5][C:3]#[N:4])=[CH:20][O:21][C:17]=2[CH:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 441195206-Bromo-1-benzofuran-3(2H)-one

Product 1

HCID 847979636-Bromo-3-benzofuranacetonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (0.7 g, 0.0173 mol) was washed with hexanes then suspended in THF (8 mL). Diethyl cyanomethylphosphonate (3.07 g, 0.0173 mol) was added dropwise and stirred 10 minutes to give clear yellow solution. A solution of 11-5 (3.38 g, 0.0158 mol) in THF (20 mL) was added dropwise, the solution stirred for 0.5 hour, then heated to reflux for 0.5 hour. A solution of 6N HCL (3.4 mL) was added and the THF was removed under vacuum. The concentrated solution was diluted with Et2O and washed with 4×30 mL 6N HCl, the ether layer was dried (MgSO4), filtered and evaporated. The residue was chromatographed (20% EtOAc/Hexanes) to give 11-6 as an orange solid.

Workup

  1. customto give clear yellow solution
  2. stirringthe solution stirred for 0.5 hour
  3. temperatureheated
  4. temperatureto reflux for 0.5 hour
  5. additionA solution of 6N HCL (3.4 mL) was added
  6. customthe THF was removed under vacuum
  7. additionThe concentrated solution was diluted with Et2O
  8. washwashed with 4×30 mL 6N HCl
  9. dry with materialthe ether layer was dried (MgSO4)
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue was chromatographed (20% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-6142c88a100f4109b17629da87f28eeb
Source dataset
uspto-grants-1998_12
Patent number
US05854245

Reaction notes

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