Dimethylformamide → HCID 10013617, compound

HRID 1182050Notes

Reaction equation

HRID 1182050 reaction equation
I[C:2]1[CH:15]=[CH:14][C:5]2[O:6][C:7]3[CH:12]=[CH:11][C:10](I)=[CH:9][C:8]=3[C:4]=2[CH:3]=1.[C:16]([Cu])#[N:17].[NH4+].[OH-].[CH3:21][N:22](C=O)C>>[CH:3]1[C:4]2[C:8]3[CH:9]=[C:10]([C:21]#[N:22])[CH:11]=[CH:12][C:7]=3[O:6][C:5]=2[CH:14]=[CH:15][C:2]=1[C:16]#[N:17]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 14923Ammonium HydroxideHCID 6345252,8-DiiododibenzofuranHCID 178418546HCID 178418546, compound

Product 1

HCID 10013617HCID 10013617, compoundYield 6%

Conditions

Temperature
160 °C

Procedure

To a solution of 2,8-Diiodo-dibenzofuran (763 mg, 1.8 mmol) in dry DMF (16 mL) add CuCN (1.1 g, 12.7 mmol), heat the mixture at 160° C. under N2 atmosphere overnight. Cool the mixture at room temperature, add NH4OH and bubble air during 4 hours. Add cool water and extract with EtOAc, dry over Na2SO4. Eliminate the solvent under reduced pressure. Purify by flash chromatography on silica gel (eluent: hexane/EtOAc 3/1) to afford the title compound (25 mg, 6%).

Workup

  1. temperatureCool the mixture at room temperature
  2. custombubble air during 4 hours
  3. additionAdd
  4. temperaturecool water
  5. extractionextract with EtOAc
  6. dry with materialdry over Na2SO4
  7. customPurify by flash chromatography on silica gel (eluent: hexane/EtOAc 3/1)

Sources & evidence

ORD record
ord-b78e8c76046042769d1bcaf6e83615fe
Source dataset
uspto-grants-2007_10
Patent number
US07288543B2

Reaction notes

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