反应 #61849

反应方程式

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

phenyl trimethylammonium tribromide

→

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

收率 118.2%

溶剂

1,2-dimethoxyethane

反应条件

后处理

1. 1
   workup.WAITat room temperature for 24 hours
2. 2
   洗涤The mixture was washed with water (500 mL)
3. 3
   萃取the aqueous phase was extracted with ethyl acetate (2×500 mL)
4. 4
   洗涤The combined organics were washed with water (2×200 mL), brine (500 mL)
5. 5
   干燥dried over magnesium sulfate
6. 6
   过滤filtered
7. 7
   其他the solvent removed under reduced pressure
8. 8
   其他to afford an orange gum
9. 9
   其他The gum was triturated with diethyl ether
10. 10
    过滤filtered

实验过程

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).

来源