Potassium Carbonate → {2-[(3-Bromo-4-chloro-benzoyl)-methyl-amino]-phenoxy}-acetic acid methyl ester

HRID 1848573Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1848573
[Br:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[Cl:19])[C:5]([N:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])[CH3:8])=[O:6].[CH3:20][O:21][C:22](=[O:25])[CH2:23]Br.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:20][O:21][C:22](=[O:25])[CH2:23][O:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[N:7]([C:5](=[O:6])[C:4]1[CH:16]=[CH:17][C:18]([Cl:19])=[C:2]([Br:1])[CH:3]=1)[CH3:8]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 686031173-bromo-4-chloro-N-(2-hydroxy-phenyl)-N-methyl-benzamide

Produkt 1

HCID 68602946{2-[(3-Bromo-4-chloro-benzoyl)-methyl-amino]-phenoxy}-acetic acid methyl esterAusbeute 92,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 3-bromo-4-chloro-N-(2-hydroxy-phenyl)-N-methyl-benzamide (442 mg, 1.3 mmol), methylbromoacetate (0.247 mL, 2.6 mmol) and K2CO3 (717 mg, 5.2 mmol) was heated in DMF (8 mL) at 80° C. for 5 hrs. After cooling to room temperature, the mixture was partitioned between ethyl acetate and water. The organic layer was separated and washed with brine, dried over Na2SO4, then purified by silica gel column chromatography eluted with ethyl acetate/hexane (1/4) to yield {2-[(3-bromo-4-chloro-benzoyl)-methyl-amino]-phenoxy}-acetic acid methyl ester (495 mg). MS [M+H]+: 413.9; tR=2.75 min. (method 1)

Aufarbeitung

  1. customthe mixture was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. custompurified by silica gel column chromatography
  6. washeluted with ethyl acetate/hexane (1/4)

Quellen und Nachweise

ORD-Eintrag
ord-ef5ff05459b841d680619bc8287c1d7e
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952161B2

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