Iodine → 2-(Prop-2-yn-1-yl)naphthalene

HRID 271592

Reaktionsgleichung

Reaktionsgleichung von HRID 271592
II.Br[C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=1.CO[CH:16]=[C:17]=[CH2:18].[Cl-].[NH4+]>C1COCC1.[Cu]Br.CCOC(C)=O.CCCCCC>[CH2:18]([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=1)[C:17]#[CH:16]

Komponenten

9

Edukt 4

HCID 807IodineHCID 113722-BromonaphthaleneHCID 25517Ammonium ChlorideHCID 1394031-Methoxypropa-1,2-diene

Produkt 1

HCID 179681822-(Prop-2-yn-1-yl)naphthaleneAusbeute 18 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24593copper(I) bromideKatalysatorHCID 8028TetrahydrofuranLösungsmittel3×HCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a suspension of Mg powder (5.3 mmol) and one piece of iodine in THF (4 ml) is added 2-bromonaphthalene (4.6 mmol) in THF (2 ml) at room temperature and the mixture is stirred at 85° C. for 0.5 h. Copper(I) bromide (0.32 mmol) is added at room temperature then methoxyallene (4.6 mmol) in THF (3 ml) is added at 0° C. and the mixture is stirred at room temperature for 2 h. The mixture is poured into saturated ammonium chloride, extracted with AcOEt. The organic layer is washed with brine, dried over sodium sulfate and concentrated. Chromatography on silica gel (n-hexane:AcOEt=20:1) gives the product in 18% yield. Rf=0.5 (n-hexane:AcOEt=10:1)

Aufarbeitung

  1. stirringthe mixture is stirred at room temperature for 2 h
  2. extractionextracted with AcOEt
  3. washThe organic layer is washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customChromatography on silica gel (n-hexane:AcOEt=20:1) gives the product in 18% yield

Quellen und Nachweise

ORD-Eintrag
ord-44d1479e542a404ba94cfc21df056244
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452886B2

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