Benzene, 1-bromo-3-nitro- → 1-(3-Nitrophenyl)pyrrolidine

HRID 2105280

反応式

HRID 2105280 の反応式
Br[C:2]1[CH:3]=[C:4]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1>[N+:8]([C:4]1[CH:3]=[C:2]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:7]=[CH:6][CH:5]=1)([O-:10])=[O:9]

参加物

5

反応物 3

HCID 11457Benzene, 1-bromo-3-nitro-HCID 31268PyrrolidineHCID 23676156Sodium t-butoxide

生成物 1

HCID 6982671-(3-Nitrophenyl)pyrrolidine収率 79%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

To a solution of 3-bromonitrobenzene (2.02 g, 10 mmol) in toluene (33 mL) and pyrrolidine (1.0 mL, 12 mmol) was added sodium t-butoxide (1.92 g, 20 mmol) and the solution was deoxygenated by passing a nitrogen through the solution at room temperature for 15 minutes. BINAP and tris(dibenzylideneacetone)dipalladium(0) complex were subsequently added as a solid and the nitrogen bubbling was continued for an additional 5 minutes. The mixture was heated at 100° C. overnight. The reaction mixture was then cooled and partitioned between water and ethyl acetate. The organic layer was washed once with brine solution and dried over anhydrous sodium sulfate. The ethyl acetate was decanted and evaporated under reduced pressure to give the desired 1-(3-nitrophenyl)pyrrolidine as a red oil (1.5 g, 79%).

後処理

  1. customthe solution was deoxygenated
  2. customat room temperature
  3. customfor 15 minutes
  4. additionBINAP and tris(dibenzylideneacetone)dipalladium(0) complex were subsequently added as a solid
  5. temperatureThe reaction mixture was then cooled
  6. custompartitioned between water and ethyl acetate
  7. washThe organic layer was washed once with brine solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe ethyl acetate was decanted
  10. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-72a5b48a680547e8a1320558772baf48
出典データセット
uspto-grants-2009_08
特許番号
US07579340B2

関連ノート

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