Water → 1-[5-Bromo-3-fluoro-2-(oxiran-2-ylmethoxy)phenyl]ethanone

HRID 38999

Reaktionsgleichung

Reaktionsgleichung von HRID 38999
[Br:1][C:2]1[CH:3]=[C:4]([F:12])[C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[CH2:13]([CH:15]1[O:17][CH2:16]1)Br.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([F:12])[C:5]([O:11][CH2:13][CH:15]2[CH2:16][O:17]2)=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 575158461-(5-Bromo-3-fluoro-2-hydroxyphenyl)ethan-1-one

Produkt 1

HCID 866529431-[5-Bromo-3-fluoro-2-(oxiran-2-ylmethoxy)phenyl]ethanoneAusbeute 85,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 1-(5-bromo-3-fluoro-2-hydroxyphenyl)ethanone (3.7 g, 15.8 mmol), epibromohydrin (2.6 ml, 31.7 mmol) and K2CO3 (3.3 g, 23.8 mmol) in DMF (20 ml) was heated at 60° C. for 1 h 50 min. The solution was brought to ambient temperature and water and EtOAc was added. The water phase was extracted with EtOAc. The combined organic phases were washed with LiCl (5%), HCl (1 N) and brine and were dried (Na2SO4) and evaporated to dryness. Purification on flash column chromatography (isooctane/EtOAc) gave the title compound (3.9 g). MS m/z (rel. intensity, 70 eV) 289 (M+, 13), 288 (M+, 14), 218 (91), 217 (bp), 81 (39), 57 (95).

Aufarbeitung

  1. customwas brought to ambient temperature
  2. extractionThe water phase was extracted with EtOAc
  3. washThe combined organic phases were washed with LiCl (5%), HCl (1 N) and brine
  4. dry with materialwere dried (Na2SO4)
  5. customevaporated to dryness
  6. customPurification on flash column chromatography (isooctane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-2c0dfc5a21934582bc955561daae8b21
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524766B2

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