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Hydrochloric Acid → HCID 67607343, Verbindung

HRID 2405463
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2405463
[CH:1]1[C:15]2=[C:16]3[C:8]([C:9]4[C:14]2=[CH:13][CH:12]=[CH:11][CH:10]=4)=[CH:7][CH:6]=[CH:5][C:4]3=[C:3](B(O)O)[CH:2]=1.Br[C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[CH:27]=[C:26]([OH:31])[CH:25]=[CH:24]2.C(=O)([O-])[O-].[Na+].[Na+].Cl>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[CH:1]1[C:15]2=[C:16]3[C:8]([C:9]4[C:14]2=[CH:13][CH:12]=[CH:11][CH:10]=4)=[CH:7][CH:6]=[CH:5][C:4]3=[C:3]([C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[CH:27]=[C:26]([OH:31])[CH:25]=[CH:24]3)[CH:2]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 271446-Bromo-2-naphthalenolHCID 23088535Fluoranthen-3-ylboronic acid

Produkt 1

HCID 67607343HCID 67607343, VerbindungAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A flask was charged with 2.7 g of fluoranthene-3-boronic acid, 2.0 g of 6-bromo-2-naphthol, 0.31 g of tetrakis(triphenylphosphine)palladium(0), 27 mL of 1,2-dimethoxyethane, and 13.5 mL of a 2 M sodium carbonate aqueous solution in an argon atmosphere. The mixture was heat refluxed with stirring for 4 hours. After cooling the reaction solution to room temperature, 2 M hydrochloric acid was added to the reaction solution so that the reaction solution had a pH in the acidic region. The reaction solution was then extracted with dichloromethane. After removing the aqueous phase, the organic phase was washed with a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. After filtering the organic phase, the solvent was evaporated under reduced pressure. The residue was dispersed and washed in dichloromethane to obtain 2.75 g of the target 6-(fluoranthen-3-yl)-2-naphthol (yield: 89%).

Aufarbeitung

  1. temperatureThe mixture was heat
  2. temperaturerefluxed
  3. extractionThe reaction solution was then extracted with dichloromethane
  4. customAfter removing the aqueous phase
  5. washthe organic phase was washed with a saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationAfter filtering the organic phase
  8. customthe solvent was evaporated under reduced pressure
  9. additionThe residue was dispersed
  10. washwashed in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-e0c1d5172c434b1f99a7e1baf092275e
Quelldatensatz
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08803420B2

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