Reaktion #61849

Reaktionsgleichung

1-naphthalen-1-yl-propan-l-one

phenyl trimethylammonium tribromide

→

2-bromo-1-naphthalen-1-yl-propan-1-one

Ausbeute 118.2%

Lösungsmittel

1,2-dimethoxyethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITat room temperature for 24 hours
2. 2
   WaschenThe mixture was washed with water (500 mL)
3. 3
   Extraktionthe aqueous phase was extracted with ethyl acetate (2×500 mL)
4. 4
   WaschenThe combined organics were washed with water (2×200 mL), brine (500 mL)
5. 5
   Trocknendried over magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Sonstigethe solvent removed under reduced pressure
8. 8
   Sonstigeto afford an orange gum
9. 9
   SonstigeThe gum was triturated with diethyl ether
10. 10
    Filtrationfiltered

Vorschrift

To a solution of 1-naphthalen-1-yl-propan-l-one (37.8 g) in 1,2-dimethoxyethane (350 mL) at 0° C. was added phenyl trimethylammonium tribromide (83 g). The mixture was stirred at 0° C. for 10 minutes and then at room temperature for 24 hours. The mixture was washed with water (500 mL) and the aqueous phase was extracted with ethyl acetate (2×500 mL). The combined organics were washed with water (2×200 mL), brine (500 mL), dried over magnesium sulfate, filtered and the solvent removed under reduced pressure to afford an orange gum. The gum was triturated with diethyl ether and filtered to afford 2-bromo-1-naphthalen-1-yl-propan-1-one (39.8 g, 74%) as an orange solid, 1H NMR (CDCl3): 1.95 (3H, d, J=6.6 Hz), 5.35 (1H, q, J=6.6 Hz), 7.45-7.60 (3H, m), 7.85-7.90 (2H, m), 8.0 (1H, d, J=8.1 Hz), 8.4 (1H, d, J=7.9 Hz).

Quelle