Sodium Acetate → 2-Bromo-4-{[(trimethysilyl)methyl]carbamoyl}benzyl acetate

HRID 1873469

Reaktionsgleichung

Reaktionsgleichung von HRID 1873469
[C:1]([O-:4])(=[O:3])[CH3:2].[Na+].[Br:6][C:7]1[CH:8]=[C:9]([CH:18]=[CH:19][C:20]=1[CH2:21]Br)[C:10]([NH:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])=[O:11]>CN(C=O)C.COC(C)(C)C>[C:1]([O:4][CH2:21][C:20]1[CH:19]=[CH:18][C:9]([C:10](=[O:11])[NH:12][CH2:13][Si:14]([CH3:16])([CH3:15])[CH3:17])=[CH:8][C:7]=1[Br:6])(=[O:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 517045Sodium AcetateHCID 580920793-bromo-4-(bromomethyl)-N-[(trimethysilyl)methyl]benzamide

Produkt 1

HCID 580920812-Bromo-4-{[(trimethysilyl)methyl]carbamoyl}benzyl acetateAusbeute 39,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 15413tert-Butyl methyl etherLösungsmittel

Versuchsvorschrift

A mixed solution of sodium acetate (2.8 g), 3-bromo-4-(bromomethyl)-N-[(trimethysilyl)methyl]benzamide (6.5 g) in DMF (30 ml) was stirred for 3 hours at 70° C. The reaction liquor was returned to room temperature and diluted with t-butyl methyl ether. The mixture was washed with water and a saturated aqueous brine, subsequently dried over magnesium sulfate. After separating the drying agent by filtration, the reaction liquor was distilled off under reduced pressure, and the resulting mixture was purified by silica gel chromatography, to obtain 2-bromo-4-{[(trimethysilyl)methyl]carbamoyl}benzyl acetate (2.4 g).

Aufarbeitung

  1. customwas returned to room temperature
  2. washThe mixture was washed with water
  3. dry with materiala saturated aqueous brine, subsequently dried over magnesium sulfate
  4. customAfter separating the drying agent
  5. filtrationby filtration
  6. distillationthe reaction liquor was distilled off under reduced pressure
  7. customthe resulting mixture was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-71f4618851ce4e068720ce3034ccca9f
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304371B2

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