2-Nitrophenol → 1-(Benzhydryloxy)-2-nitrobenzene

HRID 132589

Reaktionsgleichung

Reaktionsgleichung von HRID 132589
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].Br[CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[K].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH:12]([O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

6

Edukt 4

HCID 69472-NitrophenolHCID 11430Potassium CarbonateHCID 236603BromodiphenylmethaneHCID 5462222Potassium

Produkt 1

HCID 74341221-(Benzhydryloxy)-2-nitrobenzeneAusbeute 39,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of o-nitrophenol (2.08 g, 15.0 mmol), 1-[bromo(phenyl)methyl]benzene (3.70 g, 15.0 mmol) and potassium carbonated (K2CO3) (4.14 g, 30.0 mmol) in acetone (60 mL) was kept at reflux temperature for 5 h. The reaction mixture was cooled to room temperature, concentrated in vacuo. The residue was partitioned between dichloromethane (CH2Cl2) and water (H2O), organic layer dried over sodium sulphate (Na2SO4), filtered, concentrated. The residue was purified by silica gel flash chromatography to give subtitled compound (1.81 g).

Aufarbeitung

  1. temperatureat reflux temperature for 5 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between dichloromethane (CH2Cl2) and water (H2O), organic layer
  4. dry with materialdried over sodium sulphate (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-079031298525448db5b6e52e03b4a7e2
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07388020B2

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