Aminoacetaldehyde dimethyl acetal → 5-Bromo-2-fluorobenzylidene-2,2-dimethoxyethylamine

HRID 272777Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 272777
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[CH:7]=O.[CH3:11][O:12][CH:13]([O:16][CH3:17])[CH2:14][NH2:15]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[CH:7]=[N:15][CH2:14][CH:13]([O:16][CH3:17])[O:12][CH3:11]

Komponenten

4

Edukt 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 7363275-Bromo-2-fluorobenzaldehyde

Produkt 1

HCID 692158965-Bromo-2-fluorobenzylidene-2,2-dimethoxyethylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 5-bromo-2-fluorobenzaldehyde (15 g, 74 mmol) and 2,2-dimethoxy-ethylamine (7.77 g, 74 mmol) in toluene (142 mL) was heated to reflux for 30 minutes using a Dean-Stark trap to remove water. The solution was then concentrated under vacuum to provide 5-bromo-2-fluorobenzylidene-2,2-dimethoxyethylamine. 5-Bromo-2-fluorobenzylidene-2,2-dimethoxyethylamine and cold concentrated sulfuric acid (28 mL) were added separately, dropwise, over a period of 20 minutes to concentrated sulfuric acid (83 mL) at 140° C. The mixture was stirred at 135° C. for 30 minutes, allowed to cool, and carefully poured onto ice. Filtered to remove solids and the mixture was washed with dichloromethane. The aqueous layer was made basic by cautious addition of 50% sodium hydroxide solution, and extracted with diethyl ether. Combined ether layers were dried (MgSO4), filtered and concentrated under vacuum to provide 310 mg (2%) of the desired product. MS (ESI) m/e 226 (M+H)+.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 30 minutes
  3. customto remove water
  4. concentrationThe solution was then concentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-ea9e706d576e4638bc718a6c87ecf8c6
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456169B2

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