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

HRID 81583
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 81583
[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
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 155402-Nitrobenzenesulfonyl chlorideHCID 516893Potassium BicarbonateHCID 666660992-Amino-2-(5-bromo-2-fluoro-phenyl)-3,3-difluoro-propan-1-ol

Produkt 1

HCID 866502672-(5-Bromo-2-fluorophenyl)-2-difluoromethyl-1-(2-nitro-benzenesulfonyl)-aziridineAusbeute 37,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-93b5369ef1454877ac0728316be18f2e
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08846658B2

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