1-Iodo-4-nitrobenzene → 1,2-Dichloro-3-(4-nitrobenzyl)benzene

HRID 491514

Reaktionsgleichung

Reaktionsgleichung von HRID 491514
[Cl-].[Cl:2][C:3]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][Zn+].I[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1.[Cl-].[NH4+]>C1COCC1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>[Cl:11][C:10]1[CH:9]=[CH:8][CH:7]=[C:4]([CH2:5][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)[C:3]=1[Cl:2]

Komponenten

6

Edukt 3

HCID 124951-Iodo-4-nitrobenzeneHCID 25517Ammonium ChlorideHCID 178478089HCID 178478089, Verbindung

Produkt 1

HCID 30173791,2-Dichloro-3-(4-nitrobenzyl)benzeneAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 521585Tris(furan-2-yl)phosphaneKatalysatorHCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

Under an argon stream, bis(dibenzylidenacetone)palladium(0) (3.2 g, 5.6 mmol) and tri(2-furyl)phosphine (2.6 g, 11.2 mmol) were dissolved in THF (310 ml), the reaction mixture of 2,3-dichlorobenzylzinc chloride (421.7 mmol) in THF obtained in Reference Example 1 was added dropwise under ice-cooling through a cannula, and then a solution of 4-iodonitrobenzene (70.0 g, 281 mmol) in THF (700 ml) was added dropwise, after which the mixture was stirred at room temperature for 2 hr, saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was filtered through celite. The filtrate was concentrated under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the precipitated solid was collected by filtration on the way. The filtrate was again concentrated under reduced pressure, and the precipitated solid was collected by filtration on the way. The collected solids were combined washed with n-hexane and vacuum dried to give the object product (60.2 g, yield 76%) as a pale-brown solid.

Aufarbeitung

  1. customobtained in Reference Example 1
  2. additionwas added dropwise under ice-
  3. temperaturecooling through a cannula
  4. filtrationthe mixture was filtered through celite
  5. concentrationThe filtrate was concentrated under reduced pressure, water
  6. additionwas added to the residue
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe organic layer was washed with water and saturated brine
  9. dry with materialdried over sodium sulfate
  10. filtrationAfter filtration
  11. concentrationthe filtrate was concentrated under reduced pressure
  12. filtrationthe precipitated solid was collected by filtration on the way
  13. concentrationThe filtrate was again concentrated under reduced pressure
  14. filtrationthe precipitated solid was collected by filtration on the way
  15. washThe collected solids were combined washed with n-hexane and vacuum
  16. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8321250d960f412094fd9c88518effb1
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531554B2

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