2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 57592527、化合物

HRID 1784390ノート

反応式

HRID 1784390 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 57592527HCID 57592527、化合物収率 40.2%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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

後処理

  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)

出典と根拠

ORDレコード
ord-e63c85de40f042aaa9cf7b7f8d4fbffa
出典データセット
uspto-grants-2009_03
特許番号
US07504397B2

反応ノート

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