1,3-Difluoro-5-nitrobenzene → HCID 9887211、化合物

HRID 1901760ノート

反応式

HRID 1901760 の反応式
[CH3:1][C:2]1([CH3:18])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:11][N:12]3[CH:16]=[N:15][CH:14]=[N:13]3)[CH:9]=2)[C:4](=[O:17])[O:3]1.CC(C)([O-])C.[K+].[F:25][C:26]1[CH:27]=[C:28]([N+:33]([O-:35])=[O:34])[CH:29]=[C:30]([F:32])[CH:31]=1>CN(C)C=O>[F:25][C:26]1[CH:27]=[C:28]([N+:33]([O-:35])=[O:34])[CH:29]=[C:30]([F:32])[C:31]=1[CH:11]([N:12]1[CH:16]=[N:15][CH:14]=[N:13]1)[C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[C:4](=[O:17])[O:3][C:2]2([CH3:18])[CH3:1]

参加物

5

反応物 3

HCID 752721,3-Difluoro-5-nitrobenzeneHCID 233686093,3-dimethyl-5-[1,2,4-triazol-1-ylmethyl]-3H-isobenzofuran-1-one2 回HCID 23665647Potassium tert-butoxide

生成物 1

HCID 9887211HCID 9887211、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 3,3-dimethyl-5-[1,2,4-triazol-1-ylmethyl]-3H-isobenzofuran-1-one (4.47 g Intermediate 1) in N,N-dimethylformamide (250 ml) at 0° under nitrogen was added potassium tert-butoxide (4.53 g). After one hour 3,5-difluoronitrobenzene (3.22 g) was added and stirring continued for five hours. The reaction mixture was partitioned between water and ethyl acetate and the phases separated. The aqueous phase was extracted with ethyl acetate and the combined organic extracts were washed with water and brine, dried and then evaporated to yield a brown oil. This was purified by column chromatography on Merck 9385 silica eluting initially with dichloromethane through to a 50:1 mixture of dichloromethane:methanol to yield a brown foam. The brown foam was further purified by gradient elution HPLC (water-acetonitrile-trifluoroacetic acid) to give 5-[(2,6-difluoro-4-nitrophenyl)-1,2,4-triazol-1-ylmethyl]-3,3-dimethyl-3H-isobenzofuran-1-one as a yellow foam.

後処理

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. customthe phases separated
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washthe combined organic extracts were washed with water and brine
  5. customdried
  6. customevaporated
  7. customto yield a brown oil
  8. customThis was purified by column chromatography on Merck 9385 silica eluting initially with dichloromethane through to a 50:1 mixture of dichloromethane
  9. custommethanol to yield a brown foam
  10. customThe brown foam was further purified by gradient elution HPLC (water-acetonitrile-trifluoroacetic acid)

出典と根拠

ORDレコード
ord-1a51447f1b804e9597a1ee27a4397a91
出典データセット
uspto-grants-1996_11
特許番号
US05578630

反応ノート

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