Sodium Carbonate → 3-{[4-(4,5-Difluoro-1-benzofuran-7-yl)-phenoxy]methyl}benzoic acid

HRID 928674Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 928674
CC1(C)C(C)(C)OB([C:9]2[CH:25]=[CH:24][C:12]([O:13][CH2:14][C:15]3[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=3)[C:18]([OH:20])=[O:19])=[CH:11][CH:10]=2)O1.Br[C:28]1[C:36]2[O:35][CH:34]=[CH:33][C:32]=2[C:31]([F:37])=[C:30]([F:38])[CH:29]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[F:37][C:31]1[C:32]2[CH:33]=[CH:34][O:35][C:36]=2[C:28]([C:9]2[CH:10]=[CH:11][C:12]([O:13][CH2:14][C:15]3[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=3)[C:18]([OH:20])=[O:19])=[CH:24][CH:25]=2)=[CH:29][C:30]=1[F:38]

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 221448747-Bromo-4,5-difluorobenzofuranHCID 903844063-{[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]methyl}benzoic acid

Produkt 1

HCID 903843933-{[4-(4,5-Difluoro-1-benzofuran-7-yl)-phenoxy]methyl}benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To the compound (1.67 g, 4.72 mmol) obtained in Step 1, 7-bromo-4,5-difluoro-1-benzofuran (1.1 g, 4.72 mmol), sodium carbonate (1.0 g, 9.44 mmol), and Pd(dppf)Cl2 (catalytic amount), 1,4-dioxane (24 mL) and water (8 mL) were added, and stirred at 100° C. for 2 hours. The reaction solution was concentrated under reduced pressure. To the residue, ethyl acetate and 1 N hydrochloric acid were added and stirred. After that, the insoluble material was filtered off, and extraction was performed with ethyl acetate. The organic phase was washed with saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure, and the solid was collected by filtration.

Aufarbeitung

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionTo the residue, ethyl acetate and 1 N hydrochloric acid were added
  3. stirringstirred
  4. filtrationAfter that, the insoluble material was filtered off
  5. extractionextraction
  6. washThe organic phase was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled away under reduced pressure
  9. filtrationthe solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-bb37032e8f84428bb184d30e56bce31d
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290487B2

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