Trifluoroacetic acid → 4,5-difluoro-N-isopropyl-2-nitroaniline

HRID 502905ノート

反応式

HRID 502905 の反応式
[F:1][C:2]1[C:8]([F:9])=[CH:7][C:5]([NH2:6])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.CO[C:15](OC)([CH3:17])[CH3:16].FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[F:1][C:2]1[C:8]([F:9])=[CH:7][C:5]([NH:6][CH:15]([CH3:17])[CH3:16])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 64952,2-DimethoxypropaneHCID 1571514,5-Difluoro-2-nitroaniline

生成物 1

HCID 138524354,5-difluoro-N-isopropyl-2-nitroaniline収率 56%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

4,5-difluoro-2-nitroaniline (3.48 g, 20 mmol), 2,2-dimethoxypropane (11.9 mL, 100 mmol), and trifluoroacetic acid (1.6 mL, 21 mmol) were dissolved in toluene (40 mL) and stirred at room temperature for 1 h. A boron-pyridine complex (2.12 mL, 21 mmol) was slowly added. The reaction mixture was stirred for 20 h. The solvent was evaporated in vacuo, and the residue was taken up into water and extracted with dichloromethane. The organic extract was dried (Na2SO4) and concentrated in vacuo. The residue was chromatographed on a column of aminopropyl-silica gel eluting with hexane/ethyl acetate (30:1) to give 2.42 g (56%) of the title compound as a bright orange solid.

後処理

  1. additionA boron-pyridine complex (2.12 mL, 21 mmol) was slowly added
  2. stirringThe reaction mixture was stirred for 20 h
  3. customThe solvent was evaporated in vacuo
  4. extractionextracted with dichloromethane
  5. extractionThe organic extract
  6. dry with materialwas dried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed on a column of aminopropyl-silica gel eluting with hexane/ethyl acetate (30:1)

出典と根拠

ORDレコード
ord-aa7841e8fb0a46bc9519f68de451ff2b
出典データセット
uspto-grants-2010_08
特許番号
US07776885B2

反応ノート

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