Water → (7-Bromo-5-chloro-2,3-dihydro-1,4-benzodioxin-2-yl)methanol

HRID 39026Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 39026
C([O:4][C:5]1[CH:10]=[C:9]([Br:11])[CH:8]=[C:7]([Cl:12])[C:6]=1[O:13][CH2:14][CH:15]1[CH2:17][O:16]1)(=O)C.[OH-].[K+].O>O1CCOCC1>[Br:11][C:9]1[CH:8]=[C:7]([Cl:12])[C:6]2[O:13][CH2:14][CH:15]([CH2:17][OH:16])[O:4][C:5]=2[CH:10]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 866529535-Bromo-3-chloro-2-(oxiran-2-ylmethoxy)phenyl acetate

Produkt 1

HCID 66878380(7-Bromo-5-chloro-2,3-dihydro-1,4-benzodioxin-2-yl)methanolAusbeute 8,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 5-bromo-3-chloro-2-(oxiran-2-ylmethoxy)phenyl acetate (4.4 g, 13.7 mmol) in dioxane (20 ml) was added KOH (10%, 40 ml) at 0° C. The reaction mixture was stirred at room temperature for 2 hours. Water was added and the solution was extracted with EtOAc: The combined organic phases were washed with brine, dried (Na2SO4) and evaporated to dryness. Purification on flash column chromatography (isooctane/EtOAc) gave the title compound (0.34 g). MS m/z (rel. intensity, 70 eV) 280 (M+, bp), 278 (78), 224 (68), 222 (54), 57 (37).

Aufarbeitung

  1. extractionthe solution was extracted with EtOAc
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated to dryness
  5. customPurification on flash column chromatography (isooctane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-c63928e4aaab43de9b674b43cc9765ef
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524766B2

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