反応 #47338

反応方程式

3-(5,6,7,8-tetrahydro-naphthalen-1-yloxy)-but-2-enoic acid ethyl ester

N-bromosuccinimide

→

4-bromo-3-(5,6,7,8-tetrahydro-naphthalen-1-yloxy)-but-2-enoic acid ethyl ester

収率 71.1%

溶媒

dichloromethane

dichloromethane

反応条件

後処理

1. 1
   洗浄was washed with water (1×50 mL)
2. 2
   乾燥a saturated aqueous sodium chloride solution (1×50 mL), dried over magnesium sulfate
3. 3
   ろ過filtered
4. 4
   洗浄rinsed with dichloromethane
5. 5
   濃縮concentrated in vacuo
6. 6
   その他Purification by Analogix flash chromatography (40 g, 1-10% ethyl acetate/hexanes)

実験手順

A solution of 3-(5,6,7,8-tetrahydro-naphthalen-1-yloxy)-but-2-enoic acid ethyl ester (0.69 g, 2.65 mmol) in dichloromethane (14 mL) was treated with N-bromosuccinimide (0.50 g, 2.80 mmol) and 2,2′-azobis(2,4-dimethylvaleronitrile) (31.6 mg, 0.12 mmol). The reaction was then warmed to 45° C. where it stirred overnight. At this time, the reaction was diluted with dichloromethane (50 mL) and was washed with water (1×50 mL) and a saturated aqueous sodium chloride solution (1×50 mL), dried over magnesium sulfate, filtered, rinsed with dichloromethane, and concentrated in vacuo. Purification by Analogix flash chromatography (40 g, 1-10% ethyl acetate/hexanes) afforded impure 4-bromo-3-(5,6,7,8-tetrahydro-naphthalen-1-yloxy)-but-2-enoic acid ethyl ester (638.8 mg, 71%) as a yellow oil. The material was used without further purification.

出典