Potassium Carbonate → 2-Bromo-5-(2-morpholinoethoxy)benzaldehyde

HRID 85168

Reaktionsgleichung

Reaktionsgleichung von HRID 85168
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]=[O:5].Cl.Cl[CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[CH:6][C:3]=1[CH:4]=[O:5]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 3871792-Bromo-5-hydroxybenzaldehyde

Produkt 1

HCID 192618112-Bromo-5-(2-morpholinoethoxy)benzaldehydeAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 2-bromo-5-hydroxybenzaldehyde (62; 3 g, 15 mmol) and 4-(2-chloroethyl)morpholine hydrochloride (120; 5.6 g, 30 mmol) in DMF (75 mL) was added K2CO3 (10.3 g, 74.6 mmol). After reaction 2 h at 120° C. for 3 h, the reaction mixture was quenched by addition of water and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. Column chromatography afforded 2-bromo-5-(2-morpholinoethoxy)benzaldehyde 121 (3.3 g, 72%) as a brown solid.

Aufarbeitung

  1. customAfter reaction 2 h at 120° C. for 3 h
  2. customthe reaction mixture was quenched by addition of water
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d53fcca164194a3fbffe99193f0acfc9
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846947B2

Verknüpfte Notizen

Wird geladen…