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Dimethylformamide → 3-Chloro-4-(2-chloro-3,6-dimethyl-4-nitrophenoxy)-1,1'-biphenyl

HRID 980565
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 980565
[CH3:1][C:2]1[C:7]([Cl:8])=[C:6](Cl)[C:5]([CH3:10])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[Cl:14][C:15]1[CH:20]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:18]=[CH:17][C:16]=1[OH:27].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C1(C)C=CC=CC=1>[Cl:14][C:15]1[CH:20]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:18]=[CH:17][C:16]=1[O:27][C:6]1[C:5]([CH3:10])=[CH:4][C:3]([N+:11]([O-:13])=[O:12])=[C:2]([CH3:1])[C:7]=1[Cl:8]
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Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 70742-Chloro-4-PhenylphenolHCID 11430Potassium CarbonateHCID 137729272,3-Dichloro-1,4-dimethyl-5-nitrobenzene

Produkt 1

HCID 137729283-Chloro-4-(2-chloro-3,6-dimethyl-4-nitrophenoxy)-1,1'-biphenylAusbeute 71,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140
Toluene
Lösungsmittel

Versuchsvorschrift

Into a 100 milliliter round bottom flask equipped with a thermometer, magnetic stirrer and condenser was added 12.0 grams (0.054 moles) of 2,5-dimethyl-3,4-dichloronitrobenzene, 14.5 grams (0.071 moles) of 2-chloro-4-phenylphenol, 12.0 grams (0.087 moles) of potassium carbonate and 20 milliliters of dimethylformamide (DMF) under a nitrogen atmosphere at ambient temperature. The reaction mixture was then heated in an oil bath at a temperature of 110° C.-120° C. for a periof of 72 hours. After cooling to ambient temperature, the reaction mixture was filtered through celite and concentrated (DMF removed under vaccum) to give an amber oil. The amber oil was dissolved in toluene and thereafter washed once with 4% sodium hydroxide, once with water and finally once with a saturated aqueous sodium chloride solution. The amber oil was then dried over sodium sulfate, concentrated (toluene removed under vacuum) and stirred into a hexane-ethyl acetate mixture (6:1 volume ratio). Crystallization from the hexane-ethyl acetate mixture and filtration afforded 15.02 grams of a tan powder having a melting point of 92.5° C.-94.0° C. Elemental analysis of the tan powder indicated the following:

Aufarbeitung

  1. customInto a 100 milliliter round bottom flask equipped with a thermometer, magnetic stirrer and condenser
  2. temperatureThe reaction mixture was then heated in an oil bath at a temperature of 110° C.-120° C. for a periof of 72 hours
  3. filtrationthe reaction mixture was filtered through celite and
  4. concentrationconcentrated
  5. custom(DMF removed under vaccum)
  6. customto give an amber oil
  7. washwashed once with 4% sodium hydroxide, once with water and finally once with a saturated aqueous sodium chloride solution
  8. dry with materialThe amber oil was then dried over sodium sulfate
  9. concentrationconcentrated
  10. custom(toluene removed under vacuum)
  11. customCrystallization
  12. filtrationfrom the hexane-ethyl acetate mixture and filtration

Quellen und Nachweise

ORD-Eintrag
ord-6779a32fd76b4b16a1e8438d02af82fc
Quelldatensatz
uspto-grants-1987_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04638088

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