Benzyl Bromide → 1-(Benzyloxy)-3-bromo-5-nitrobenzene

HRID 1010682Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1010682
[Br:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.C([O-])([O-])=O.[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC(C)=O.O>[CH2:18]([O:11][C:4]1[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=[C:2]([Br:1])[CH:3]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

6

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 104889843-Bromo-5-nitrophenol

Produkt 1

HCID 147841491-(Benzyloxy)-3-bromo-5-nitrobenzeneAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To an ice-cold solution of 3-bromo-5-nitro-phenol (21.0 g, 96.33 mmol) in acetone (420.0 mL) was added K2CO3 (40.0 g, 289.41 mmol) followed by addition of benzyl bromide (17.20 mL, 144.40 mmol). The resulting reaction mixture was stirred at room temperature for 2 h. The reaction mixture was then diluted with water and extracted with EtOAc (3×250.0 mL). The combined organics was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude was purified over silica gel (100-200 M, 5% EtOAc-Hexane) to get the desired product (27.0 g, 91%).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. extractionextracted with EtOAc (3×250.0 mL)
  3. dry with materialThe combined organics was dried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude was purified over silica gel (100-200 M, 5% EtOAc-Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-ff08803fcabb4f589fe9e7ca45a5448e
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977340B2

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