Diethyl Ether → 2-Bromo-1-(3,5-dibromo-4-hydroxyphenyl)ethanone

HRID 1943709Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1943709
[Br:1][C:2]1[CH:3]=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([Br:9])[C:7]=1[OH:8].C(OCC)C.[Br:18]Br.C(=O)([O-])O.[Na+]>O1CCCC1.O.C(O)(=O)C>[Br:18][CH2:11][C:10]([C:4]1[CH:3]=[C:2]([Br:1])[C:7]([OH:8])=[C:6]([Br:9])[CH:5]=1)=[O:12]

Komponenten

8

Edukt 4

HCID 3283Diethyl EtherHCID 24408BromineHCID 761581-(3,5-Dibromo-4-hydroxyphenyl)ethan-1-oneHCID 516892Sodium Bicarbonate

Produkt 1

HCID 37844242-Bromo-1-(3,5-dibromo-4-hydroxyphenyl)ethanoneAusbeute 51,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In a 100 ml flask, 1-(3,5-dibromo-4-hydroxy-phenyl)-ethanone (1.2 g, 4.082 mmol) was dissolved in a solvent of anhydrous tetrahydrofuran: anhydrous diethyl ether (1:1, 12 ml). Acetic acid (0.4 ml) and bromine (2.1 ml, 4.082 mmol) were added thereto dropwise under nitrogen atmosphere and then stirred at room temperature for 2 hours. After completion of the reaction by adding water dropwise, the mixture was adjusted to pH 8 to 9 with saturated solution of sodium hydrogen carbonate and extracted with ethyl acetate, and the combined organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica eluting with a solvent of n-hexane:ethyl acetate=2:1. The fractions containing the product were collected and evaporated to obtain 2-bromo-1-(3,5-dibromo-4-hydroxy-phenyl)-ethanone as white solid (785 mg, 51.5%).

Aufarbeitung

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. dry with materialthe combined organic layer was dried over anhydrous sodium sulfate (Na2SO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica eluting with a solvent of n-hexane
  7. additionThe fractions containing the product
  8. customwere collected
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-eb0e151f73594bc38493e1d46bed4648
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394792B2

Notizen zur Reaktion

Wird geladen…