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Dimethylformamide → Methyl 5-(benzyloxy)-2-bromo-2',4'-difluorobiphenyl-4-carboxylate

HRID 531074
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 531074
[Br:1]N1C(=O)NC(=O)N(Br)C1=O.CN(C=O)C.[CH2:17]([O:24][C:25]1[CH:26]=[C:27]([C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][C:36]=2[F:42])[CH:28]=[CH:29][C:30]=1[C:31]([O:33][CH3:34])=[O:32])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O>[CH2:17]([O:24][C:25]1[C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][C:28]([Br:1])=[C:27]([C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][C:36]=2[F:42])[CH:26]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1
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Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 192912Dibromoisocyanuric acidHCID 117992142Methyl 3-(benzyloxy)-2',4'-difluorobiphenyl-4-carboxylate

Produkt 1

HCID 117992213Methyl 5-(benzyloxy)-2-bromo-2',4'-difluorobiphenyl-4-carboxylateAusbeute 141,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Dibromoisocyanuric acid (15.9 g) was added at room temperature to a DMF (150 mL) solution of methyl 3-(benzyloxy)-2′,4′-difluorobiphenyl-4-carboxylate (28.0 g), and the mixture was stirred overnight at the same temperature as above. Water was added to the reaction mixture at room temperature, followed by extraction with ethyl acetate. The obtained organic layer was washed with water and saturated saline in this order 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 (34.0 g).

Aufarbeitung

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe obtained organic layer was washed with water and saturated saline in this order
  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-9a24129254124ee68ae64bbec05d2c46
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09353108B2

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