Reaktion #1180646

Reaktionsgleichung

Compound 73-1

3-(1-naphthyl)-1-propanol

triphenylphosphine

N-bromosuccinimide

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product

Ausbeute 90.2%

1-(3-bromopropyl)naphthalene

Ausbeute 90.2%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   Temperaturcooling for 2 hr
3. 3
   WaschenThe reaction mixture was washed with water and saturated brine
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   SonstigeThe solvent was evaporated under reduced pressure
6. 6
   workup.ADDITIONDiethyl ether (100 ml) was added
7. 7
   Filtrationthe precipitated triphenylphosphine oxide was filtered off
8. 8
   EinengenThe concentrate of the filtrate
9. 9
   Sonstigewas purified by silica gel column chromatography

Vorschrift

Compound 73-1 (4.70 g) was dissolved in methylene chloride (50 ml), triphenylphosphine (7.13 g) and N-bromosuccinimide (4.84 g) were added under ice-cooling, and the mixture was stirred under ice-cooling for 2 hr, and further at room temperature for 15 hr. The reaction mixture was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. Diethyl ether (100 ml) was added, and the precipitated triphenylphosphine oxide was filtered off. The concentrate of the filtrate was purified by silica gel column chromatography to give the object product (5.67 g) as a colorless oil.

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