Benzyl Bromide → 1-Benzyloxy-3-methyl-2-nitrobenzene

HRID 1193484

Reaktionsgleichung

Reaktionsgleichung von HRID 1193484
[CH3:1][C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[C:4]([OH:8])[CH:5]=[CH:6][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>CN(C=O)C>[CH2:18]([O:8][C:4]1[C:3]([N+:9]([O-:11])=[O:10])=[C:2]([CH3:1])[CH:7]=[CH:6][CH:5]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 210263-Methyl-2-nitrophenol

Produkt 1

HCID 33441871-Benzyloxy-3-methyl-2-nitrobenzeneAusbeute 88,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 3-methyl-2-nitrophenol (50 g, 0.326 mol), K2CO3 (45 g, 0.326 mol) and benzylbromide (61.4 g, 42.6 mL, 0.359 mol) in dry DMF (200 mL) was stirred at 90° C. for 3 hours under nitrogen. Most of the DMF was removed at reduced pressure and the residue was partitioned between water (300 mL) and ether (300 mL). The organic layer was washed with brine and dried (Na2SO4). Removal of the solvent provided (70 g, 88%) of 3-benzyloxy-2-nitrotoluene as an orange oil.

Aufarbeitung

  1. customMost of the DMF was removed at reduced pressure
  2. customthe residue was partitioned between water (300 mL) and ether (300 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customRemoval of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-a704537da871413fb26b32dab55ba06d
Quelldatensatz
uspto-grants-1989_03
Patentnummer
US04810699

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