1-Bromonaphthalene → 1-Cyclopropylnaphthalene

HRID 551342

Reaktionsgleichung

Reaktionsgleichung von HRID 551342
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.Br[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1>O1CCCC1.Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[CH:1]1([C:15]2[C:16]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:3][CH2:2]1

Komponenten

5

Edukt 2

HCID 70011-BromonaphthaleneHCID 178418630HCID 178418630, Verbindung

Produkt 1

HCID 146686931-CyclopropylnaphthaleneAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418745HCID 178418745, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Cyclopropylmagnesium bromide (150 mL, 0.5 M in tetrahydrofuran) was slowly added to a solution of 1-bromo-naphthalene (10 g, 50 mmol) and [1,3-bis(diphenylphosphino)propane]dichloronickel(II) in tetrahydrofuran (10 mL) stirred at 0° C. The reaction mixture was stirred at room temperature for 16 hours and the solvent was evaporated under reduced pressure. EtOAc and ammonium chloride in water were added. After extraction, the organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography to yield 1-cyclopropyl-naphthalene (6.4 g, 76%).

Aufarbeitung

  1. stirringThe reaction mixture was stirred at room temperature for 16 hours
  2. customthe solvent was evaporated under reduced pressure
  3. additionEtOAc and ammonium chloride in water were added
  4. extractionAfter extraction
  5. dry with materialthe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-13db7488c62f433e84dcd70a8261dcfa
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947721B2

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