Ethylenediamine → Benzofuran-4-carbonitrile

HRID 911339Notes

Reaction equation

HRID 911339 reaction equation
Br[C:2]1[C:7]2[CH:8]=[CH:9][O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Cu][C:12]#[N:13].C(N)CN>CN(C=O)C>[O:10]1[C:6]2=[CH:5][CH:4]=[CH:3][C:2]([C:12]#[N:13])=[C:7]2[CH:8]=[CH:9]1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 151587214-Bromo-1-benzofuranHCID 178418546HCID 178418546, compound

Product 1

HCID 13307980Benzofuran-4-carbonitrileYield 41.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combine 4-bromo-benzofuran (1.0 g, 5.07 mmol), copper(I) cyanide (0.9 g, 10.2 mmol), anhydrous DMF (16 ml) and reflux for 17 h. Cool the reaction mixture to ambient temperature, treat with 50% (v/v) aqueous ethylenediamine (25 mL). Extract the reaction mixture with diethyl ether (3×15 mL), combine the organic extracts, wash with brine (15 mL) and dry over anhydrous Na2SO4. Evaporate the solvent and purify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1 and 4:1) to obtain the desired intermediate as a colorless oil (0.3 g, 39%).

Workup

  1. extractionExtract the reaction mixture with diethyl ether (3×15 mL)
  2. washwash with brine (15 mL)
  3. dry with materialdry over anhydrous Na2SO4
  4. customEvaporate the solvent
  5. custompurify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1 and 4:1)

Sources & evidence

ORD record
ord-8608ae5ff3e44768be742618054e124d
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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