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Trifluoroacetic anhydride → 2-Cyano-4,5-dimethoxy-3-(2,2,2-trifluoroethoxy)nitrobenzene

HRID 1004034
ノート
印刷プレビュー

反応式

HRID 1004034 の反応式
[N+:1]([O-:4])([O-])=[O:2].[NH4+].FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH3:19][O:20][C:21]1[C:22]([O:31][CH2:32][C:33]([F:36])([F:35])[F:34])=[C:23]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[C:24]#[N:25]>ClCCl>[C:24]([C:23]1[C:22]([O:31][CH2:32][C:33]([F:34])([F:35])[F:36])=[C:21]([O:20][CH3:19])[C:28]([O:29][CH3:30])=[CH:27][C:26]=1[N+:1]([O-:4])=[O:2])#[N:25]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 9845Trifluoroacetic anhydrideHCID 22985Ammonium nitrateHCID 184706363,4-Dimethoxy-2-(2,2,2,-trifluoroethoxy)benzonitrile

生成物 1

HCID 184706192-Cyano-4,5-dimethoxy-3-(2,2,2-trifluoroethoxy)nitrobenzene収率 73%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Ammonium nitrate (2.82 g, 0.035 mol) and trifluoroacetic anhydride (12.4 ml, 0.088 mol) were added to a solution of 3,4-dimethoxy-2-(2,2,2,-trifluorethoxy)benzonitrile in dichloromethane. The temperature was maintained between 20° C. and 30° C. for 2 hours, after which time the reaction mixture was washed with saturated aqueous sodium bicarbonate solution. The organic layer was separated, dried (MgSO4) and evaporated under reduced pressure. Trituration with diethyl ether followed by filtration afforded a first crop of product. The filtrate was purified on silica gel, eluting with dichloromethane to afford the subtitle compound as a colourless solid (combined yield 6.56 g, 73%). Rf 0.31 (ethyl acetate:hexane 20:80, v/v). MS m/z 324 (MNH4)+

後処理

  1. temperatureThe temperature was maintained between 20° C. and 30° C. for 2 hours
  2. washafter which time the reaction mixture was washed with saturated aqueous sodium bicarbonate solution
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. filtrationTrituration with diethyl ether followed by filtration
  7. customafforded a first crop of product
  8. customThe filtrate was purified on silica gel
  9. washeluting with dichloromethane

出典と根拠

ORDレコード
ord-bccc93803f264ed7ab3f513011f3ef46
出典データセット
uspto-grants-2000_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06048864

反応ノート

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