Water → 1-(Benzyloxy)-3-bromo-2-fluorobenzene

HRID 1879040Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1879040
[Br:1][C:2]1[C:3]([F:9])=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CC(C)=O.C(OCC)(=O)C>[CH2:16]([O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[C:3]=1[F:9])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 184012573-Bromo-2-fluorophenol

Produkt 1

HCID 574388031-(Benzyloxy)-3-bromo-2-fluorobenzeneAusbeute 105,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 3-bromo-2-fluorophenol (1.8 g, 9.42 mmol) in acetone (25 ml) was added sodium carbonate (2.55 g, 20 mmol) and the mixture was stirred for 5 min. Benzylbromide (1.2 ml, 10.3 mmol) was added and the reaction mixture was heated at reflux for 20 h. Water (50 ml) and ethyl acetate (50 ml) was added and the phases were separated. The aqueous phase was extracted with ethyl acetate (2×50 ml) and the combined organic phases was dried (MgSO4) and evaporated under reduced pressure to give an oil. The residue was purified by flash column chromatography (isooctane/ethyl acetate, 5:1) to give the title compound (2.8 g). MS m/z (rel. intensity, 70 eV) 282 (M+, 2), 280 (M+, 2), 163 (2), 161 (2), 91 (bp).

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 20 h
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted with ethyl acetate (2×50 ml)
  5. dry with materialthe combined organic phases was dried (MgSO4)
  6. customevaporated under reduced pressure
  7. customto give an oil
  8. customThe residue was purified by flash column chromatography (isooctane/ethyl acetate, 5:1)

Quellen und Nachweise

ORD-Eintrag
ord-fd67c3fdea1c4817a008e4751f724304
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08314126B2

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