Water → (7-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol

HRID 984483

Reaktionsgleichung

Reaktionsgleichung von HRID 984483
[Br:1][C:2]1[CH:9]=[C:6](C=O)[C:5]([OH:10])=[CH:4][CH:3]=1.[CH2:11]([CH:13]1[O:15][CH2:14]1)Cl.C([O-])([O-])=[O:17].[K+].[K+].O>CN(C=O)C>[OH:17][CH2:14][CH:13]1[CH2:11][O:10][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:9][C:6]=2[O:15]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 728635-Bromosalicylaldehyde

Produkt 1

HCID 233965(7-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanolAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a stirred solution of 5-bromosalicylaldehyde (5.0 g, 24.9 mmol), and epichlorohydrin (5.6 mL, 72.1 mmol) in 20 mL of DMF at 80° C. was added K2CO3 slowly in portions. The resulting mixture was then heated at 90° C. for 3 h. Reaction was then stopped, water was added, extracted with diethyl ether. The organic extracts were washed with water, brine, dried over Na2SO4, concentrated in vacuo. The residue was purified on a SiO2 flash column chromatography eluting with 15-30% EtOAc/hexanes to give 2.82 g (44%) of the title compound as colorless oil.

Aufarbeitung

  1. customReaction
  2. extractionextracted with diethyl ether
  3. washThe organic extracts were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified on a SiO2 flash column chromatography
  7. washeluting with 15-30% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-1dc99065235e46769bedd783d4257b57
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06867203B2

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