Reaktion #67024

Reaktionsgleichung

Cyclopropylmagnesium bromide

1-bromonaphthalene

→

1-cyclopropylnaphthalene

Ausbeute 76.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction mixture stirred at room temperature for 16 hours
2. 2
   SonstigeThe solvent was removed under reduced pressure and ethyl acetate and aqueous ammonium chloride
3. 3
   workup.ADDITIONwere added
4. 4
   ExtraktionAfter extraction
5. 5
   Trocknenthe organic layer was dried over sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   SonstigeThe residue was purified by silica gel chromatography

Vorschrift

Cyclopropylmagnesium bromide (150 mL, 0.5M in tetrahydrofuran) was slowly added to a solution of 1-bromonaphthalene (10 g, 50 mmol) and [1,3-bis(diphenylphosphino)propane]dichloro nickel (II) in tetrahydrofuran (10 mL) stirred at 0° C., and the reaction mixture stirred at room temperature for 16 hours. The solvent was removed under reduced pressure and ethyl acetate and aqueous ammonium chloride 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-cyclopropylnaphthalene (6.4 g, 76%).

Quelle