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2-Nitrobenzenesulfonyl chloride → 2-(5-Bromo-2-fluorophenyl)-2-difluoromethyl-1-(2-nitro-benzenesulfonyl)-aziridine

HRID 81583
ノート
印刷プレビュー

反応式

HRID 81583 の反応式
[NH2:1][C:2]([C:8]1[CH:13]=[C:12]([Br:14])[CH:11]=[CH:10][C:9]=1[F:15])([CH:5]([F:7])[F:6])[CH2:3]O.[N+:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25](Cl)(=[O:27])=[O:26])([O-:18])=[O:17].C(=O)([O-])O.[K+]>C(#N)C>[Br:14][C:12]1[CH:11]=[CH:10][C:9]([F:15])=[C:8]([C:2]2([CH:5]([F:7])[F:6])[CH2:3][N:1]2[S:25]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N+:16]([O-:18])=[O:17])(=[O:26])=[O:27])[CH:13]=1
参加物反応条件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 155402-Nitrobenzenesulfonyl chlorideHCID 516893Potassium BicarbonateHCID 666660992-Amino-2-(5-bromo-2-fluoro-phenyl)-3,3-difluoro-propan-1-ol

生成物 1

HCID 866502672-(5-Bromo-2-fluorophenyl)-2-difluoromethyl-1-(2-nitro-benzenesulfonyl)-aziridine収率 37.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

2-Amino-2-(5-bromo-2-fluoro-phenyl)-3,3-difluoro-propan-1-ol (13.04 g, 45.9 mmol) [examples 42 step d)] was dissolved in 261 mL acetonitrile, 2-nitrobenzenesulfonyl chloride (22.38 g, 101 mmol) and potassium hydrogencarbonate (13.79 g, 138 mmol) were added. The mixture was heated to 80° C. and stirred over night. After this period, the reaction mixture was cooled down and partitioned between saturated aqueous NaHCO3 solution and TBME. The layers were separated, washed with brine and TBME. The combined organic layers were dried over MgSO4.H2O and evaporated. The crude product was purified on a silica gel column by eluting with hexane/dichloromethane 2/1->1/2 to give 7.71 g of the title compound as white crystals.

後処理

  1. waitAfter this period
  2. temperaturethe reaction mixture was cooled down
  3. custompartitioned between saturated aqueous NaHCO3 solution and TBME
  4. customThe layers were separated
  5. washwashed with brine and TBME
  6. dry with materialThe combined organic layers were dried over MgSO4.H2O
  7. customevaporated
  8. customThe crude product was purified on a silica gel column
  9. washby eluting with hexane/dichloromethane 2/1->1/2

出典と根拠

ORDレコード
ord-93b5369ef1454877ac0728316be18f2e
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08846658B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート