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Dimethylformamide → Methyl 2-bromo-4'-fluoro-5-isopropoxy-[1,1'-biphenyl]-4-carboxylate

HRID 531001
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 531001
[Br:1]N1C(=O)NC(=O)N(Br)C1=O.[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([O:27][CH3:28])=[O:26])=[C:21]([O:29][CH:30]([CH3:32])[CH3:31])[CH:20]=2)=[CH:15][CH:14]=1.CN(C=O)C>O>[Br:1][C:24]1[CH:23]=[C:22]([C:25]([O:27][CH3:28])=[O:26])[C:21]([O:29][CH:30]([CH3:32])[CH3:31])=[CH:20][C:19]=1[C:16]1[CH:15]=[CH:14][C:13]([F:12])=[CH:18][CH:17]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 192912Dibromoisocyanuric acidHCID 117992325Methyl 4'-fluoro-3-isopropoxybiphenyl-4-carboxylate

Produkt 1

HCID 117992274Methyl 2-bromo-4'-fluoro-5-isopropoxy-[1,1'-biphenyl]-4-carboxylateAusbeute 127,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Dibromoisocyanuric acid (4.60 g) was added to a mixture of methyl 4′-fluoro-3-isopropoxybiphenyl-4-carboxylate (6.61 g) and DMF (60 mL), and the resultant mixture was stirred at room temperature for 5 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (7.53 g).

Aufarbeitung

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe obtained organic layer was washed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-8e514bd6613b4ad8b90595d05459b622
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09353108B2

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