2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 57592527, compound

HRID 1784390Notes

Reaction equation

HRID 1784390 reaction equation
[Br:1][C:2]1[O:3][C:4](Br)=[CH:5][CH:6]=1.C([Li])CCC.[Cl:13][C:14]1[N:19]=[CH:18][CH:17]=[CH:16][N:15]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C(OCC)C.CCOC(C)=O>[Br:1][C:2]1[O:3][C:4]([C:16]2[CH:17]=[CH:18][N:19]=[C:14]([Cl:13])[N:15]=2)=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 744042-ChloropyrimidineHCID 108788462,5-dibromofuranHCID 178418339Butyllithium

Product 1

HCID 57592527HCID 57592527, compoundYield 40.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cooled (−78° C.) solution of 2,5-dibromofurane (3.06 g, 8.88 mmol) in anhydrous diethyl ether (50 ml) was added n-Butyllithium (3.9 ml of 2.5M solution in Hexanes, 9.77 mmol). The mixture was stirred at this temperature for 90 minutes before the addition of 2-chloropyrimidine. The mixture was stirred for a further 30 minutes before being warmed to room temperature and stirred for further 2 hours. DDQ (2 g, 8.88 mmol) was them added to the solution which was stirred for 30 minutes before being concentrated in vacuo to give a thick brown syrup. The syrup was dissolved in EtOAc and washed with saturated sodium carbonated solution. The organic extract was removed, dried (MgSO4), filtered and concentrated in vacuo to give a crude residue which was purified by flash chromatography (SiO2) (100% hexane going to 7:2—hexane:EtOAc) to give the title compound (3.06 g, 40.20%) in pure form. m/z (LC-MSW, ESP):346 [M+H]+, R/T=4.41 mins

Workup

  1. stirringstirred for further 2 hours
  2. additionadded to the solution which
  3. stirringwas stirred for 30 minutes
  4. concentrationbefore being concentrated in vacuo
  5. customto give a thick brown syrup
  6. washwashed with saturated sodium carbonated solution
  7. extractionThe organic extract
  8. customwas removed
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customto give a crude residue which
  13. customwas purified by flash chromatography (SiO2) (100% hexane going to 7:2—hexane:EtOAc)

Sources & evidence

ORD record
ord-e63c85de40f042aaa9cf7b7f8d4fbffa
Source dataset
uspto-grants-2009_03
Patent number
US07504397B2

Reaction notes

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