Benzyl Bromide → 2-(Benzyloxy)-1,3-dichloro-5-nitrobenzene

HRID 883816

Reaktionsgleichung

Reaktionsgleichung von HRID 883816
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:9][C:10]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[C:12]([Cl:19])[C:11]=1[OH:20].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:20][C:11]1[C:12]([Cl:19])=[CH:13][C:14]([N+:16]([O-:18])=[O:17])=[CH:15][C:10]=1[Cl:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 120662,6-Dichloro-4-nitrophenol

Produkt 1

HCID 595097642-(Benzyloxy)-1,3-dichloro-5-nitrobenzeneAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

Benzyl bromide (17.25 mL, 144 mmol) was added to a stirring solution of 2,6-dichloro-4-nitrophenol (5 g, 24 mmol) and potassium carbonate (13.3 g, 96 mmol) in acetone (30 mL). The mixture was heated to 75° C. for 12 h before being cooled to room temperature and poured into ice-water (100 mL). The mixture was extracted with chloroform (200 mL), washed with brine (100 mL) and the combined organic layers were dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (9:1, hexane/dichloromethane) to afford 2-(benzyloxy)-1,3-dichloro-5-nitrobenzene as a white solid (99% yield).

Aufarbeitung

  1. temperaturebefore being cooled to room temperature
  2. extractionThe mixture was extracted with chloroform (200 mL)
  3. washwashed with brine (100 mL)
  4. dry with materialthe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (9:1, hexane/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-adf458a830bd4170b2b9a7d04b267dfc
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236984B2

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